Hexane → HCID 54260529, compound

Participants

Reaction Conditions

Reaction Steps

To 103 mg of 60% sodium hydride, prewashed with hexane, in 10 ml of dimethyl sulfoxide was added 500 mg of the title product of Example 100. The mixture was stirred at 40° C. until gas evolution ceased, and then 290 mg of sodium chloroacetate was added, the resulting mixture stirred at room temperature overnight and then at 80° for 1 hour. After cooling, the mixture was partitioned between diethyl ether and dilute aqueous hydrochloric acid, the aqueous layer further extracted with ether, the combined organic extracts washed with several portions of water and then brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using 30% ethyl acetate-2% acetic acid-68% hexane gave the title compound (155 mg) as a pure white crystalline solid, DSC 96.5° C.

Provenance & Evidence