Diisopropylamine → HCID 13596438, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.5 ml of diisopropylamine in 75 ml of tetrahydrofuran were added dropwise 135 ml of a 1.5 M solution of butyl lithium in hexane, 75 ml of hexamethylphosphoramide (HMPA) and 6.15 ml of propiolic acid, successively, at -50° C., the mixture was allowed to heat to -10° C. over a period of 2 hours. To it was added dropwise 27.2 ml of 1,5-dibromopentane at -25° to -30° C., the solution allowed to heat to room temperature over a period of 2 hours, and stirred for one hour. The reaction mixture was poured into 500 ml of ice-water, extracted with methylene chloride, the extract washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in diethyl ether, there was added diazomethane-etherate until the solution was coloured pale yellow. After concentration under reduced pressure, the residue was purified by column chromatography on silica gel using chloroform as eluent to give 4.05 g of the subtitle compound having the following physical characteristics:

Provenance & Evidence