Ethyl Thioglycolate → Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]butanoate

Participants

Reaction Conditions

Reaction Steps

Sodium metal (4.3 g, 0.18 mol) was added cautiously in small portions to ethanol (150 mL). After the sodium completely dissolved, the mixture was cooled to 0° C. and ethyl 2-sulfanylacetate (21.9 g, 0.18 mol), was added. Ethyl 4-chlorobutanoate (27.4 g, 0.18 mol) was then added slowly and the resulting mixture stirred overnight at rt. The solid was filtered off, and then the filtrate concentrated under reduced pressure. The oil obtained was partitioned between water and ethyl acetate. The organic layer was collected, dried over anhydrous Na2SO4 and concentrated under vacuum to give the desired ethyl 4-((ethoxycarbonyl)methylthio)butanoate (40.2 g, 95%) as colorless oil. The crude material was used without further purification in the follow step.

Provenance & Evidence