Ethyl Acetate → HCID 178451153, compound

Participants

Reaction Conditions

Reaction Steps

Thiazole (100 mg, 1.175 mmol) was dissolved in THF (11 mL) and cooled to a temperature of −78° C. N-butyllithium (2 M in hexanes, 0.587 mL, 1.175 mmol) was added and the mixture was allowed to stir for 30 minutes at −78° C. A solution of trans-butyl 4-acetylcyclohexanecarboxylate (319 mg, 1.410 mmol) in THF (1 mL) was then added to the mixture, and the combined solution was allowed to stir for 1 hour at −78° C. The reaction was diluted with water, warmed to 23° C., and transferred to a separatory funnel containing EtOAc. The layers were separated and the organic layer was washed with water, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel to afford butyl trans-4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate. MS ESI calc'd. for C16H26NO3S [M+H]+ 312. found 312.

Provenance & Evidence