7-Methoxybenzofuran

S3: In a 3L four-necked flask equipped with a mechanical stirrer and a thermometer, 263 g (1. Omol, 2. Oeq) tetrabutylammonium fluoride was added, L00g 4A molecular sieves and 1.5 L tetrahydrofuran, Mix at 20 ° C to 25 ° C for 1 hour. Then 151 g (0.5 mol, 1. eqq)3-methoxy-2-triisopropylsiloxyphenylacetylene was added to the mixture, The reaction was terminated by heating to 45 ° C to 50 ° C for 4 hours. Filtration, filtrate concentration, To the residue was added 250 mL of cyclohexane and the organic phase was washed with 100 mL of 5percent dilute hydrochloric acid, 1 OOmL water and 1 OOmL saturated brine, separated, the organic phase was dried over anhydrous sodium sulfate, The filtrate was concentrated under reduced pressure to give 64.8 g7-methoxybenzofuran, yield 88percent, purity 99percent (HPLC).Heating7-methoxy-2-benzofuran-2-carboxylic acid XVI (5g, 0.026mol) add to 30 ml Quinoline . then addcopper0.2g) , heating to reflux 2 hours. The mixture will be through the diatomite filterand use EtOAc to washing . R emove solvent, and then by column chromatography25percent EtOAc- Hexaneobtain yellow oillike substance. 2. 45gyield 64percentTo a round bottom flask were added 7-methoxy-2-benzofuran-2- carboxylic acid (5.0 g, 0.026 mol), copper (0.2 g, 3 mmol), and quinoline (30 mL). The reaction mixture was heated at reflux for 2 h. The mixture was filtered through Celite and washed with EtOAc, concentrated to dryness, and purified by flash column chromatography to yield the title compound (2.45 g, 64percent yield) as a yellow oil. MS (ESI): mass calcd. for CTo a round bottom flask were added 7-methoxy-2-benzofuran-2-carboxylic acid (5.0 g, 0.026 mol), copper (0.2 g, 3 mmol), and quinoline (30 mL). The reaction mixture was heated at reflux for 2 h. The mixture was filtered through Celite and washed with EtOAc, concentrated to dryness, and purified by flash column chromatography to yield the title compound (2.45 g, 64percent yield) as a yellow oil. MS (ESI) : mass calcd. for C REFERENCE EXAMPLE 54 General procedure: A 25 mL round-bottomed flask was charged with 2-aryloxyacetaldehyde diethyl acetals (1 mmol), Sn-b (0.1 g), andtrifluorotoluene (10 mL). The mixture was stirred under refluxingcondition and monitored by GC. Upon completion, the mixture wascooled to room temperature, and the catalyst Sn-b was filtrate off.The filter cake was washed with trifluorotoluene (10 mL3). Thecombined filtratewas concentrated under vacuum. The residuewaspurified by flash column chromatography on SiO2 (petroleumether/ethyl acetate) to afford the desired 2, 3-unsubstituted benzo[b]furans.Reference Example 213 A suspension of 7-methoxybenzofuran-2-carboxylicacid (11.04 g) and copper powder (1.83 g) in quinoline (200 ml) was refluxed under nitrogen atmosphere for 2 hours and cooled, and to the suspension was added 2N hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with 2N hydrochloric acid (8 times), water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give dark brown oil of 7-methoxybenzofuran (8.19 g). 1H-NMR (200 MHz, CDCl3) delta 4.02 (s, 3H), 6.77 (d, 1H, J=1.8 Hz), 6.81 (dd, 1H, J=6.8, 2.2 Hz), 7.16 (t, 1H, J=7.8 Hz), 7.21 (d, 1H, J=5.6 Hz), 7.63 (d, 1H, J=2.2 Hz).S3: In a 3L four-necked flask equipped with a mechanical stirrer and a thermometer, 263 g (1. Omol, 2. Oeq) tetrabutylammonium fluoride was added, L00g 4A molecular sieves and 1.5 L tetrahydrofuran, Mix at 20 C to 25 C for 1 hour. Then 151 g (0.5 mol, 1. eqq)3-methoxy-2-triisopropylsiloxyphenylacetylene was added to the mixture, The reaction was terminated by heating to 45 C to 50 C for 4 hours. Filtration, filtrate concentration, To the residue was added 250 mL of cyclohexane and the organic phase was washed with 100 mL of 5% dilute hydrochloric acid, 1 OOmL water and 1 OOmL saturated brine, separated, the organic phase was dried over anhydrous sodium sulfate, The filtrate was concentrated under reduced pressure to give 64.8 g

Molecular Weight:148.16
XLogP3:2.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:148.052429494
Monoisotopic Mass:148.052429494
Topological Polar Surface Area:22.4
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes