Methyl Ethyl Ketone → HCID 14219944, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-3-butyne-2-ol (15 g, 0.178 mol) in tetrahydrofuran (150 ml) is cooled to −78° C. under a nitrogen atmosphere and n-butyl lithium (1.6 molar solution in hexanes, 244 ml, 0.39 mol) is added slowly over 1.5-2.0 hours. The reaction mixture is stirred for 1 hour at −78° C. and to this mixture a solution of 2-butanone (24 ml, 0.266 mol) in tetrahydrofuran (24 ml) is added. The reaction mixture is stirred at −78° C. for one hour and allowed to come to ambient temperature and stirred at ambient temperature for 2-3 hours. The reaction mixture is cooled to 10° C., quenched with ice cold water. The aqueous phase is extracted with dichloromethane (3×150 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2,5-dimethylhept-3-yne-2,5-diol (15 g) as colourless oil.

Provenance & Evidence