Potassium Hydroxide → HCID 57249165, compound

Participants

Reaction Steps

30 g of pulverized potassium hydroxide is added to a solution of 7.65 g of 9,10-didehydroergoline-8-carboxylic acid methyl ester (28.5 mmol) and 1.22 g of tetrabutylammonium hydrogen sulfate in 900 ml of methylene chloride, and then 125 ml of trichloroethyl chloroformate is added dropwise thereto. After 15 minutes, the mixture is cooled in an ice bath, gently combined with about 300 ml of saturated sodium bicarbonate solution, and stirred for one hour. After extraction with chloroform, this phase is washed with water, dried over magnesium sulfate, and evaporated. The crude product is chromatographed on silica gel with chloroform and methanol, yielding 13.85 g (79% of theory) of 9,10-didehydro-1,6-bis(2,2,2-trichloroethoxycarbonyl)-8-ergolinecarboxylic acid methyl ester as an oily mixture of isomers.

Provenance & Evidence