Hydrochloric Acid → (5-Methoxy-1-benzofuran-2-yl)methanol

To a solution of 5 methoxybenzofuran-2-carboxylic acid (10.0 gm; 52 mmoles) in THF (300 mL) cooled at -78° C. was added diisobutylaluminium hydride (120 ml, 182 mmoles) via a syringe. The reaction mixture temperature was raised to room temperature and the solution was stirred for 3 hours. The mixture was poured into a saturated solution of ammonium chloride (500 ml) and stirred 15 minutes then was acidified with HCl 6N. This mixture was extracted with ethyl acetate (2×500 ml). The combined organic extract was concentrated in vacuo. The residue was chromatographed on silica gel using 30% ethyl acetate in hexane to yield 5-methoxy-2-hydroxymethylbenzofuran, E8, (6.5 gm, 71%).