Sodium hydride → (RS)-4-(Ethylthio)-2-phenylbutanoic Acid

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Reaction Steps

(RS)-4-Bromo-2-phenylbutanoic acid (prepared as described in Farmaco (pavia) Ed. Sci. 355 21(5) 1966) (2.43 g) in dimethylformamide (5 ml) was added to a stirred suspension of sodium hydride (0.33 g, as an 80% dispersion in oil) and ethanethiol sodium salt (1.26 g) in dimethylformamide (15 ml) at 0° C. The mixture was warmed to room temperature, stirred for 2 hours and evaporated. The residue was partitioned between water and ethylacetate, the aqueous layer acidified with concentrated hydrochloric acid and extracted with ethylacetate. The organic layer was dried over sodium sulphate and evaporated to give the title compound (2 g, 89%) as an oil.

Provenance & Evidence