Sodium hydride → 2-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl Ester

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Reaction Conditions

Reaction Steps

A solution of 3-oxothiobutyric acid S-tert-butyl ester (7.5 g) in 1,2-dimethoxyethane (10 mL) was added to a stirred suspension of sodium hydride (60% in oil, 1.9 g) in 1,2-dimethoxyethane (100 mL) at −20° C. The mixture was warmed to 0° C. for 10 minutes and then a solution of 1-bromomethyl-4-methanesulfonylbenzene (12.9 g) in 1,2-dimethoxyethane (30 mL) was added dropwise over a period of 10 minutes. The resulting mixture was warmed to room temperature over 30 minutes and then stirred at this temperature for 17 hours. The mixture was diluted with saturated aqueous ammonium chloride solution (70 mL) and the phases separated. The aqueous phase was extracted with diethyl ether and the combined organic phases were dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume) gave title compound, 7.1 g.

Provenance & Evidence