2-Cyclohexylethanol → 4-(2-Cyclohexylethoxy)-3-oxobutanoic acid 3,3-diphenylpropyl ester

Participants

Reaction Steps

2.5 ml of a solution of 610 mg (1.84 mmol) of (3,3-diphenylpropane-1-yl)4-chloroacetoacetate in THF was added dropwise to a suspension of 158 mg (3.95 mmol) of sodium hydride (60% oily) in 5 ml of THF at 0° C., and they were stirred at room temperature for 20 minutes. An alkoxide solution previously prepared by adding 397 mg (3.09 mmol) of 2-cyclohexylethanol to 5 ml of a solution of 134 mg (3.36 mmol) of sodium hydride (60% oily) in THF was added to the obtained mixture at 0° C., and they were stirred at room temperature for 3 nights. THF was evaporated under reduced pressure. Water was added to the residue. The obtained mixture was washed with ethyl acetate. The aqueous layer was acidified with 2 N hydrochloric acid. After the extraction with ethyl acetate followed by drying over sodium sulfate, ethyl acetate was evaporated under reduced pressure to obtain the title compound.

Provenance & Evidence