Sodium hydride → HCID 131726621, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (956 mg, 60% in oil, 23.9 mmol) in THF (60 mL) cooled at 0° C. was added dropwise trimethyl phosphonoacetate (3.87 mL, 4.35 g, 23.9 mmol). The mixture was stirred for 20 mn at 0° C. and cyclopentylacetone (2.22 mL, 2.00 g, 15.9 mmol) was added dropwise. The solution was warmed to 25° C., then refluxed for 2 h, and poured in a solution of brine (100 mL). The reaction mixture was extracted with ethyl acetate (2×50 mL) and the combined organic phase was dried over sodium sulfate and concentrated to give the ester (2.87 g, 99%) as a mixture of E and Z isomers 3:1. MS (m/z) 182 (M).

Provenance & Evidence