Trimethyl phosphonoacetate → HCID 54096970, compound

Participants

Reaction Steps

Trimethyl phosphonoacetate (328 mg) is added dropwise to a solution of potassium tert-butoxide (220 mg) in THF (5 ml) of 0° under a nitrogen atmosphere. The solution is stirred at 0° for 20 minutes, then cooled to -78°. A solution of 3-(5-formylpentyl)-2-(3-pyridyl)-1-methylindole (450 mg) in THF (5 ml) is added dropwise over 15 minutes. The mixture is kept at -78° for 15 minutes, then the cooling bath is removed. The mixture is stirred overnight at room temperature, then diluted with water (25 ml) and extracted with diethyl ether (3×25 ml). The combined extracts are washed with saturated sodium bicarbonate, then brine, and dried over anhydrous magnesium sulfate. Concentration in vacuo yields the α,β unsaturated ester, 3-(7-methoxycarbonylhept-6-enyl)-2-(3-pyridyl)-1-methylindole.

Provenance & Evidence