Sulfuric Acid → 3-Trifluoromethyl-2-penten-1-ol

Participants

Reaction Steps

To a solution of 10 g of a mixture of (E) and (Z) isomers of ethyl 3-trifluoromethyl-2-pentenoate in 100 ml of tetrahydrofuran was added dropwise 100 ml of diisobutylaluminum hydride (1.02M solution in hexane) under ice-cooling, and then stirred at the same temperature for 2 hours. To the reaction mixture was added diluted sulfuric acid and then extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain crude 3-trifluoromethyl-2-penten-1-ol as a mixture of (E) and (Z) isomers.

Provenance & Evidence