Hydrochloric Acid → HCID 21541510, compound

Participants

Reaction Steps

A toluene solution of diethylaluminum cyanide was prepared by reacting 15.7 g of triethylaluminum with 4.1 g of hydrocyanic acid in 300 ml of toluene. Into the obtained toluene solution of diethylaluminium cyanide was added a mixture of 15.4 g of 2-(6'-carbomethoxy-hexyl)-3-methoxy-4-hydroxy-2-cyclopenten-1-one prepared in Step 2 under cooling and the resultant mixture was allowed to stand for 2 hours at room temperature. The reaction mixture was poured into diluted hydrochloric acid under cooling. The organic layer thus formed was separated, and the aqueous layer was extracted with ether. The combined organic layers were washed with aqueous sodium bicarbonate solution and then water and dried over magnesium sulfate. After evaporation of the solvent, the residual oil was purified using chromatography on silica gel to provide 11.6 g of 2-(6'-carbomethoxyhexyl)-3-cyano-4-hydroxy-2-cyclopenten-1-one as an oily material.

Provenance & Evidence