Ethanol → tert-Butyl 2-Hydroxy-2-(4-(hydroxymethyl)phenyl)ethyl(methyl)carbamate

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Reaction Steps

tert-Butyl 2-(4-formylphenyl)-2-hydroxyethyl(methyl)carbamate (1.808 g, 6.48 mmol) was dissolved in dry THF (50 ml) and absolute ethanol (10 ml) then cooled in an ice bath. Sodium borohydride (0.25 g, 6.61 mmol) was added then after 1 hr the solvent was evaporated. The residue was treated with satd. ammonium chloride solution (15 ml), water (35 ml) and chloroform (50 ml). The aqueous layer was extracted with additional chloroform (2×50 ml). The combined organics were washed with brine (30 ml), dried (magnesium sulfate), filtered and evaporated to afford the product as a white gum (1.82 g).

Provenance & Evidence