Valtrate → Baldrinal

Participants

Reaction Steps

Valtrate (1) (9.2 g) was dissolved in 20 ml of chloroform at room temperature. In another flask, 20 g of trifluoroacetic acid was dissolved in 40 ml of chloroform. This second solution then was added to the first solution. The clear solution became dark green/blue after stirring for 5 minutes. Chloroform (60 ml) was added to the reaction mixture, and the reaction mixture was washed with water until a pH of 4 was reached. Sodium chloride with 0.5% NaHCO3 (125 mL) was added to neutralize the mixture. Baldrinal (2, 1.1 g) was collected as a yellow liquid using column chromatography with 8:2 hexanes:ethyl acetate as solvent.

Provenance & Evidence