2-Benzofurancarboxaldehyde, 5-methoxy- → (5-Methoxy-1-benzofuran-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Compound 24 (3.5 g, 19.9 mmol) was dissolved in EtOH (20 mL). NaBH4 (957 mg, 25.87 mmol) was added portionwise at 0° C., with vigorous stirring. The suspension was stirred at 0° C. for 15 min and then at room temperature for 1.5 h. Solvent was evaporated off in-vacuo. The residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (2:1) to give 25 (3.0 g, 85%) as a white solid. 1H NMR (500 MHz, CDCl3): δ: 7.36 (1H, d, J=8.90 Hz, H-7), 7.02 (1H, d, J=2.6, H-4), 6.90 (1H, dd, J=6.30 & 2.60, H-6), 6.61 (1H, s, H-3), 4.76 (2H, s, 2-CH2), 3.86 (3H, s, OCH3), 2.16 (1H, bs, OH). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ: 113.07 (C-7), 111.69 (C-6), 104.34 (C-4), 103.60 (C-3), 58.24 (CH2), 55.92 (OCH3).

Provenance & Evidence