Sodium hydride → HCID 54458864, compound

Participants

Reaction Steps

3.185 g of dimethylphosphonomethoxyacetic acid methyl ester are added dropwise at room temperature to a suspension of 360 mg of sodium hydride in 10 cc of absolute tetrahydrofuran in the absence of moisture. After stirring at room temperature for 30 minutes, a solution of 3.284 g of (S)-3-ethyl-3-formyl-N-[2-(5-methoxy-indol-3-yl)-ethyl]-2-piperidone in 10 cc of absolute tetrahydrofuran is added dropwise at room temperature to the reaction solution while stirring for 30 minutes. The reaction mixture is subsequently stirred at room temperature for a further 2 hours, poured on ice and extracted with methylene chloride. The organic phases are dried and concentrated. A yellowish oil, consisting of a mixture of the Z and E isomers of 3-{(S)-3-ethyl-1-[2-(5-methoxy-indol-3-yl)ethyl]-2-oxo-3-piperidyl}-2-methoxy-propenoic acid methyl ester, is obtained.

Provenance & Evidence