Hydrochloric Acid → HCID 13455829, compound

Participants

Reaction Conditions

Reaction Steps

Acetylene, purified by passing first through a trap cooled with ice and then through a trap containing concentrated sulfuric acid, is bubbled through 40 ml of anhydrous THF for 1 hour. Ethylmagnesium bromide (40 ml, 1M in THF, 40 mmol) is then added dropwise. After the addition, the solution is evaporated under reduced pressure and the residue is taken up with 80 ml of methylene chloride (CH2Cl2) distilled over P2O5. The ketone prepared in Example 1 (386 mg; 1.2 mmol), dissolved in CH2Cl2 (150 ml), is added dropwise to this solution, cooled to -40° C. The reaction mixture is stirred for 1 hour at between -40° C. and -20° C., then hydrolyzed with a 0.1N solution of hydrochloric acid and then extracted in the conventional manner with methylene chloride. Chromatography under pressure (CH2Cl2) makes it possible to separate the unreacted starting ketone (148 mg; 38%) from the ethynylcarbinol formed (165 mg; 43%).

Provenance & Evidence