Product
  • Product
  • Supplier
  • Inquiry

    EN

    Home > Pharmaceutical Intermediates > Sleep Disorder Agents > 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur...
    1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... structure

    1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur...

    • CAS No:

      196597-78-1

    • Formula:

      C11H10O2

    • China Export:

      From 2018.11 to 2019.11, total export volume of 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... from China was 71,354,697KG while total export value was $983,463,687. The biggest proportion of exporting volume in the last 12 months was 10.42% in 2019.03.

    Request for Quotation

    Basic Attributes

    • 196597-78-1

    • C11H10O2

    • 174.2

    • 174.068085

    • 26.3

    • 1.7

    • ZZUIZMWFNOKNLN-UHFFFAOYSA-N

    • 2

    • 0

    • 0.36

    • 0

    Characteristics

    • 1.3±0.1 g/cm3

    • 149-151ºC

    • 334.156°C at 760 mmHg

    • 165.6±21.4 °C

    • 1.624

    Safety Information

    • 2932999099

    Production Methods

    4, 5-Dibromo-1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (280 kg, 843mol), anhydrous sodium acetate (173 kg, 2109 mol), methanol (6384 L) were mixed, and the reaction system was replaced with nitrogen. Then, to the reaction mixture was added 10percent Pd/C (30.8 kg, as dry weight), and pressurized with hydrogen to 0.29 to 0.49 MPa, and catalytically reduced at about 40°C for 8 hrs with stirring at such a stirring rate that the gas-liquid overall mass transfer coefficient KReference Example 6 To a suspension of 4, 5-dibromo-l, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (720 g, 2.15 moles) in methanol (6.60 lit.) and acetic acid (1.5 lit.) was added 10percent palladium on activated carbon (150 g, 50percent hydrous) followed by addition of sodium acetate (500 g, 6.09 moles). The reaction mixture was stirred at room temperature for 2 hours under hydrogen atmosphere (5 kg/cm6, 7-dihydro-8H-indeno-[5, 4-b]furan-8-one of the formula (IV) (2.0 g, 11.6 mmol) was dissolved in a solvent mixture (40 ml ethanol, 20 ml tetrahydrofuran and 12 drops of triethylamine). The stirred solution was hydrogenated for 24 hours at 35 °C/0.6-0.7 MPa over Pd-C (500 mg, 5 percent Pd-C (w/w)). The progress of reaction was monitored with HPLC. After the reaction was completed, the hydrogen gas was released, Pd-C was filtered off and the product was washed with 20 ml THF. After removal of the solvent under vacuum, recrystallization from ethanol afforded 1 , 2, 6, 7-tetrahydro-8 - -indeno- [5, 4-b]furan-8-one of the formula (I) as light yellow solid (yield 62 percent, 99.6 HPLC purity). 4, 5-Dibromo-1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (280 kg, 843mol), anhydrous sodium acetate (173 kg, 2109 mol), methanol (6384 L) were mixed, and the reaction system was replaced with nitrogen. Then, to the reaction mixture was added 10percent Pd/C (30.8 kg, as dry weight), and pressurized with hydrogen to 0.29 to 0.49 MPa, and catalytically reduced at about 40°C for 8 hrs with stirring at such a stirring rate that the gas-liquid overall mass transfer coefficient KLa(1/hr) is about 15. The catalyst was filtered, and the filtrate was concentrated under reduced pressure, and further water was added to the residue, followed by concentrating under reduced pressure to substitute the solvent, cooling and stirring for 1 hr to mature. The crystallization solution was filtered to give wet crystals of title compound (amount 127 kg as dry weight, yield 86.6percent). The content of dimer in the wet crystals was less than 0.1percent by weight.15 g of compound I and 1.6 g of 10percent Pd / C were dissolved in 200 mL of acetic acid and passed through hydrogen. The reaction was complete by GC-MS. The reaction was complete and filtered. The filtrate was spin-dried in ethyl acetate, washed once with water, dried over anhydrous magnesium sulfate, Spin-dried and recrystallized from ethanol to give 6.68 g of compound IIC in a yield of 85.0percent.Reference Example 6 1, 2, 6, 7-Tetrahydro-8H-indeno[5, 4-b]furan-8-one To a suspension of 4, 5-dibromo-1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (18.4 g, 55.4 mmols) in methanol (400 mL) was added 10percent Palladium on activated carbon (2.0 g, 50percent hydrous) followed by sodium acetate (12.6 g, 154 mmols). The mixture was stirred at 40° C. for 1.5 hours under hydrogen atmosphere (4 kgf/cm2). The catalyst was filtered off and the filtrate was concentrated under reduced pressure. Crystals were collected by filtration, washed with water and recrystallized successively with methanol:water=5:1 to obtain 8.0 g (yield: 83percent) of the title compound.To a suspension of 4, 5-dibromo-l, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (720 g, 2.15 moles) in methanol (6.60 lit.) and acetic acid (1.5 lit.) was added 10percent palladium on activated carbon (150 g, 50percent hydrous) followed by addition of sodium acetate (500 g, 6.09 moles). The reaction mixture was stirred at room temperature for 2 hours under hydrogen atmosphere (5 kg/cm2). After the completion of reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The obtained crystals were collected by filtration, washed with water (3 lit.) and recrystallized with methanol-water (5:1) to obtain 318 g (83percent yield) of the title compound.Reference Example 6: Synthesis of 1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one 4, 5-Dibromo-1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (23.3 g, 70.3 mmol), anhydrous sodium acetate (14.4 g, 175.5 mmol) and methanol (373 g) were mixed and, after replacing the atmosphere in the system with nitrogen, 10percent Pd/C (1.28 g) (as dry) was added to the mixture and the system was pressurized with hydrogen up to 490 kPa with stirring. The catalytic reduction reaction was conducted at 40OEC under pressure of 294 to 490 kPa for 2 hours. The catalyst was removed by filtration, the filtrate was concentrated under reduced pressure and water was further added thereto, followed by concentration under reduced pressure to effect replacement of the solvent. The mixture was cooled and stirred for one hour to effect aging. The deposited crystals were collected by filtration to obtain the title compound (yield: 14.4 g, 86.5percent).REFERENCE EXAMPLE 6 Synthesis of 1, 2, 6, 7-Tetrahydro-8H-indeno[5, 4-b]furan-8-one 4, 5-Dibromo-1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (23.3 g, 70.3 mmol), anhydrous sodium acetate (14.4 g, 175.5 mmol) and methanol (373 g) were mixed and, after replacing the atmosphere in the system with nitrogen, 10percent Pd/C (1.28 g) (as dry) was added to the mixture and the system was pressurized with hydrogen up to 490 kPa with stirring. The catalytic reduction reaction was conducted at 40° C. under pressure of 294 to 490 kPa for 2 hours. The catalyst was removed by filtration, the filtrate was concentrated under reduced pressure and water was further added thereto, followed by concentration under reduced pressure to effect replacement of the solvent. The mixture was cooled and stirred for one hour to effect aging. The deposited crystals were collected by filtration to obtain the title compound (yield: 14.4 g, 86.5percent).Alternate process for the preparation of 1 , 2, 6, 7-tetrahydro-8H- indano[5, 4-b]furan-8-one (FORMULA Vl, wherein 1^* represents a single bond); 70 g of 4, 5-dibromo-1 , 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one ofFormula VII (wherein represents a single bond), methanol (1600 ml) and sodium acetate (44 g) and 28 g of raney chloride were charged into an autoclave and the resultant reaction mixture was maintained at about 10 kg/cm2 hydrogen pressures at 5O0C. After the completion of the reaction the reaction mixture was filtered through celite followed by washing the celite with (50 ml) of methanol. The resultant filtrate was distilled off completely at below 5O0C under vacuum. The obtained crude was cooled to 260C and water was added followed by stirring for solid separation. The separated solid was filtered and washed with water. The obtained solid was dried under vacuum at 7O0C to a constant weight to afford 30.0 g of the title compound.EXAMPLE 8: Preparation of 1 , 2, 6, 7-tetrahydro-8H-indano[5, 4-b]furan-8-one (FORMULA Vl, wherein ii:^^ represents a single bond); 70 g of 4, 5-dibromo-1 , 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one of Formula VII (wherein represents a single bond ) was charged into an autoclave-containing methanol (1600 ml) and sodium acetate (44 g). 8.75 g of 10percent palladium carbon was charged and the resultant reaction mixture was maintained at about 3.0-3.7 kg/cm2 hydrogen pressures at about 420C. After the completion of the reaction the reaction mixture was filtered through celite followed by washing the celite with 500 ml of methanol. The resultant filtrate was distilled off completely at below 64OoC under vacuum to afford crude. The obtained crude was cooled to 260C and 700 ml of water was added followed by stirring for solid separation. The separated solid was filtered and washed with 200 ml of water. The obtained solid was dried under vacuum at 5O0C to a constant weight to afford 33 g of the title compound.4, 5-Dibromo-1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (23.3 g, 70.3 mmol), anhydrous sodium acetate (14.4 g, 175.5 mmol) and methanol (373 g) were mixed and, after replacing the atmosphere in the system with nitrogen, 10percent Pd/C (1.28 g) (as dry) was added to the mixture and the system was pressurized with hydrogen up to 490 kPa with stirring. The catalytic reduction reaction was conducted at 40° C. under pressure of 294 to 490 kPa for 2 hours. The catalyst was removed by filtration, the filtrate was concentrated under reduced pressure and water was further added thereto, followed by concentration under reduced pressure to effect replacement of the solvent. The mixture was cooled and stirred for one hour to effect aging. The deposited crystals were collected by filtration to obtain the title compound (yield: 14.4 g, 86.5percent). [Purification Process] The wet crystals (13.2 g, 55.7 mmol), activated carbon Shirasagi A-1 (0.5 g) and methanol (320 g) were mixed, stirred under reflux for one hour and then filtered. The filtrate was concentrated under reduced pressure, refluxed for one hour and then cooled. Water (24 g) was added dropwise thereto with cooling and, after aging for one hour, the deposit was collected by filtration and then dried under reduced pressure to obtain the title compound (yield: 9.4 g, 96.0percent).Reference Example 7 (E)-(1, 6, 7, 8-Tetrahydro-2H-indeno[5, 4-b]furan-8-ylidene)acetonitrile To a solution of To a solution of l, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-one (300 g, 1.72 moles) and diethyl (cyanomethyl) phosphonate (365.8 g, 2.06 moles) in toluene (7.5 lit.) was added drop-wise 28percent sodium methoxide in methanol (399 g, 2.06 moles). After stirring for 2 hours at room temperature, water (3 lit.) was added to the reaction mixture to separate the organic layer which was washed with water (1.2 lit.) and concentrated under reduced pressure. The obtained crystals were collected by filtration to obtain 300 g (yield: 88 percent) of the title compound.To a solution of toluene (184 g), To a solution of toluene (184 g), Example 4:Preparation of (E)-(1 , 6, 7, 8-Tetrahydro-2H-indeno[5, 4-b]furan-8-ylidene)acetonitrile (Via)ViaNaH (0.5 g, 1.2 eq) was suspended into a solution of toluene (15 ml), reaction was cooled down to O0C. Diethyl cyanomethanephosphonate (2 ml, 1.2 eq) was added and the reaction was stirred for 1 hour. 6, 7-dihydro-1 H-indeno[5, 4-b]furan-8(2H)-one (1.8 g, 10.3 mmol) in suspension in toluene (25 ml) was added slowly. MeOH (0.5 ml) was added and the reaction was warmed up to room temperature and stirred for 3 hours. Reaction was quenched with water (25 ml). Phases were separated, aqueous phase was re-extracted with toluene (15 ml). Combined organic phases were washed with brine, dried over MgSO4 and concentrated. Purification by flash chromatography gave compound Via (amount 1.56 g, yield 76.5percent).Reference Example 19 (E)-(1, 6, 7, 8-tetrahydro-2H-indeno[5, 4-b]furan-8-ylidene)acetonitrile In the same manner as in Reference Example 7, the target compound was obtained from Diethyl cyanomethylphosphonate (12.20 g) was added drop-wise at 0° to 5°C to a suspension of sodium hydride (2.75 g) in tetrahydrofuran (70 mL) and Nu, Nu'- dimethylpropyleneurea (10 mL). The mixture was stirred for 10 minutes and 1, 2, 6, 7- tetrahydro-8H-indeno[5, 4-b]furan-8-one (10 g) was added to the mixture whilemaintaining temperature at 5° to 10°C. The reaction mixture was stirred for 2 hours, poured into water (200 mL) and filtered. The solid obtained was dried under vacuum at 40° to 45°C and crystallized from methanol (50 mL) to obtain the title compound.Yield: 10.4 g

    More

    Material and Products

    China 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... Export Data

    Data referenced from General Administration of Customs,P.R.China

    2018.11-2019.11 China - America  1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... Export Data

    From 2018.11 to 2019.11, total export volume of 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... from China to America was 12,519,343KG while total export value was $152,357,070. The biggest proportion of exporting volume in the last 12 months was 11.16% in 2019.05.

    2018.11-2019.11 China 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... Export Data

    From 2018.11 to 2019.11, total export volume of 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... from China was 71,354,697KG while total export value was $983,463,687. The biggest proportion of exporting volume in the last 12 months was 10.42% in 2019.03.

    2018.11-2019.11 TOP10 Purchasing Countries' Export Data of Chinese 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur...

    From 2018.11 to 2019.11, China has exported 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]fur... to 126 countries in total. Country ranks by import volume from high to low is America, India, Korea, Netherlands, Japan, Singapore, Mexico, United Kingdom, Indonesia, Russia. The highest export volume was China to America, accounting for 9.57% of the total volume of China.

    Check Export Data for More Purchasing Countries

    Purchasing Country Export Volume(KG) Export Percentage Export Value($)

    America

    12,519,343

    9.57%

    152,357,070

    India

    6,082,851

    4.65%

    198,525,587

    Korea

    5,824,989

    4.45%

    39,808,708

    Netherlands

    5,058,931

    3.87%

    35,773,327

    Japan

    4,830,184

    3.69%

    60,127,676

    Singapore

    2,716,006

    2.08%

    18,756,256

    Mexico

    2,337,835

    1.79%

    36,753,347

    United Kingdom

    2,274,907

    1.74%

    26,159,805

    Indonesia

    2,112,320

    1.61%

    30,587,799

    Russia

    2,080,255

    1.59%

    12,685,057

    Italy

    2,070,338

    1.58%

    14,767,637

    France

    2,005,573

    1.53%

    15,491,550

    Brazil

    1,872,801

    1.43%

    26,516,488

    Germany

    1,641,210

    1.25%

    30,703,692

    Spain

    1,506,916

    1.15%

    19,823,450

    Turkey

    1,397,977

    1.07%

    6,020,976

    Pakistan

    1,300,300

    0.99%

    20,701,163

    Australia

    1,257,784

    0.96%

    10,714,674

    Belgium

    1,247,800

    0.95%

    14,995,602

    Poland

    1,009,705

    0.77%

    6,513,743

    Canada

    899,406

    0.69%

    14,866,452

    Vietnam

    799,979

    0.61%

    9,613,820

    Bangladesh

    678,954

    0.52%

    10,950,151

    Thailand

    655,027

    0.50%

    11,921,937

    Taiwan

    639,547

    0.49%

    10,951,875

    Iran

    636,709

    0.49%

    4,363,336

    Saudi Arabia

    624,818

    0.48%

    6,222,831

    Malaysia

    590,056

    0.45%

    3,051,935

    Argentina

    394,770

    0.30%

    7,063,276

    Ireland

    371,206

    0.28%

    4,817,789

    Suggestions
    Email:
    Message:
    Send Message