2-(2-Bromoethoxy)tetrahydro-2H-pyran

Clear pale yellow liquid

To a solution of 2-bromoethanol 24 (50.0 g, 40 mmol) in methylene chloride (500 mL) cooled to 0 To as solution of2-bromoethanol (3.8 g, 30.0 mmol) and DHP (2.5 g, 30.0 mmol) inDCM (50 mL), was added TsOH (380.0 mg, 2.2 mmol) in portions and the mixture was stirred atroom temperature for 2 hrs. The reaction was concentrated and purified by silica gel column(PE/EA ' 50/l) to g1ve 2-(2-bromoethoxy)tetrahydro-2H-pyran (5.6 g, yield: 89 percent) as acolorless oil.Step 5 2-(2-Bromoethoxy)tetrahydro-2H-pyran:; 3, 4-Dihydro-2H-pyran (7.80 g, 92.72 mmol) was added dropwise to a mixture of 2-bromoethanol (10.00 g, 80.03 mmol), p-toluenesulfonic acid monohydrate (1.52 g, 7.99 mmol) and dry dichloromethane (50 mL) at about 0° C. The reaction mixture was stirred at ambient temperature for about 24 hours. The volatiles were removed in vacuo to provide a crude residue. The residue was purified by silica gel column chromatography (diethyl ether) to afford the title product as a dark oil which was used in the next step without further purification (13.00 g, 78percent). Intermediate 2 2-(2-bromoethoxy)tetrahydro-2H-pyran To a solution of 2-bromoethanol (15 g, 0.12 mol) in DCM (150 mL) was added PPTS (891 mg, 3.6 mmol), then dihydropyran (10.6 g, 0.126 mol) was added dropwise at 0 °C. The mixture was stirred at room temperature for 4 h. It was partitioned between DCM and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (50: 1) to give 2-(2-bromoethoxy)tetrahydro-2H-pyran(18.0 g, 72.0percent yield) as a light yellow oil.2-Bromoethanol (2 g, 16.0 mmol, 1 eq), 3, 4-dihydropyran (2.15 g, 25.6 mmol, 1.6 eq) was dissolved in 40 mL of dichloromethane and PPTS (0.402 g , 1.6 mmol, 0.1 eq) was added and the reaction was stirred at room temperature for 8 hours, The reaction was carried out. After completion of the reaction, the reaction was complete and the reaction was complete. The organic phase was separated by the addition of 10 mL of water. The organic phase was dried over anhydrous sodium sulfate and dried. Column chromatography PE: EA (v / v) = 20: 1 gave 2.3 g of product , The yield was 69percent.To a solution of 2-bromo ethanol 13-1 (5 g, 40 mmol) in DCM (250 mL) was added /?-toluenesulfonic acid (760 mg, 4 mmol) followed by dihydropyran (4.3 mL, 48 mmol) at 0 °C and stirred at RT for 5 hr. The reaction mixture was diluted with EtOAc (100 mL) washed with water (100 mL), brine (10 mL) and dried over NaStep 1 (Synthesis of Compound 1-2) (0075) Compound 1-1 (12.5 g, 100 mmol) was dissolved in methanol (30 mL), and THP (12.6 g, 150 mmol), p-TsOH (250 mg, 1.3 mmol) were added at room temperature, stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure and then purified by silica gel column chromatography with an eluent system (PE: EtOAc=30:1) to obtain the product 1-2, yield: 80percent. (0076)

2-Hydroxyethyl derivatives, 1 furan-condensed compound, 2 indole 3, and pyrazole for preparing cardiolipin analogs.

Molecular Weight:209.08
XLogP3:1.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:208.00989
Monoisotopic Mass:208.00989
Topological Polar Surface Area:18.5
Heavy Atom Count:10
Complexity:87.7
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes