Benzaldehyde → 1-phenylbut-3-yn-1-ol

Participants

Reaction Conditions

Reaction Steps

To 0.425 ml (1.43 mmol) of tetraisopropoxytitanium and 10 ml of ethyl ether solution of propargyl bromide (0.127 ml, 1.43 mmol) was added dropwise at −50° C. 1.90 ml of 1.43M ethyl ether solution containing isopropylmagnesium bromide (2.72 mmol). After stirring at −50° C. to −40° C. for 1 hour, the reaction liquid was given 0.102 ml (1.0 mmol) of benzaldehyde at −40° C. and heated to −20° C. over 30 minutes. With 1N hydrochloric acid added, the solution was heated to room temperature and separated into layers. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate. After drying with anhydrous magnesium sulfate, the solution was freed of solvent by vacuum distillation. The residues were purified by silica gel chromatography. Thus there was obtained 124 mg of 4-phenyl-1-butyn-4-ol (85% yields based on benzaldehyde).

Provenance & Evidence