Sodium borohydride → 1-[5-(Benzyloxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropan-1-ol

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Reaction Steps

1-[5-(Benzyloxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropan-1-one (11.7 g) synthesized in the above-mentioned (1) was dissolved in a tetrahydrofuran (150 mL) and methanol (15 mL), and sodium borohydride (90%, 3.0 g) was added under ice-cooling. The ice bath was removed, the reaction mixture was stirred at room temperature for 2 hr. The mixture was ice-cooled again, water (10 mL) and 1N hydrochloric acid (100 mL) were carefully added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (11.3 g, quantitative) as a pale-yellow oil.

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