Ethyl formate → 3-(m-Tolyl)propiolaldehyde

Participants

Reaction Conditions

Reaction Steps

1.56 g of 3-ethynyltoluene was dissolved in 20 ml of ethyl ether, and with stirring at -70° C., 8.5 ml of 1.5M n-butyllithium-hexane solution and 1.2 ml of ethyl formate were added. The mixture was stirred at the same temperature for 20 minutes. The reaction mixture was poured into ice water, and the organic layer was separated. The solvent was evaporated to give 900 mg (yield 47%) of 3-(3-methylphenyl)-2-propynaldehyde as a colorless oil.

Provenance & Evidence