Sodium hydride → HCID 14421669, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 12.5 g of (2,4-dihydroxy-3-propylphenyl)(2-hydroxyphenyl)methanone in 460 ml of dimethylformamide were added 1.83 g of 60% sodium hydride in oil. The mixture was stirred for one hour under a nitrogen atmosphere. A solution of 4.9 ml of 6-bromohexanenitrile in a small volume of dimethylformamide was added. The reaction was stirred at 60° C. overnight, cooled to 25° C., and poured into a diethyl ether/water mixture. The layers were separated, and the organic layer was washed three times with water, dried over magnesium sulfate, filtered, and evaporated. Purification by high pressure liquid chromatography over silica gel eluting with a 15-35% ethyl acetate/hexane gradient, and evaporation of the desired fractions provided 6.1 g of the desired title product. Crystallization from ethyl acetate/hexane provided material with a melting point of 62°-63° C.

Provenance & Evidence