Sodium Cyanide → 4-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

Participants

Reaction Conditions

Reaction Steps

Dissolve 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester (10 g, 32.4 mmol) in anhydrous hexamethylphosphoramide (160 mL) and treat with sodium cyanide (1.59 g, 32.4 mmol). Heat at 70° C. for 48 hours, cool and dilute with saturated ammonium chloride (300 mL). Extract with ethyl ether (400 mL), wash with water (2×300 mL), then brine (300 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (5→10% methanol/chloroform) to give the title compound (1.09 g).

Provenance & Evidence