CO[C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:12]([OH:14])=O.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].Cl.C1C[O:31][CH2:30]C1>>[CH3:30][O:31][C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([CH2:12][OH:14])=[CH:3][C:7]=2[CH:8]=1To 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%).
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