Ethyl 4,4,4-trifluoroacetoacetate → Diethyl Trifluoroacetylglutarate

Participants

Reaction Steps

To a solution of NaOEt (0.217 mol) in EtOH (prepared from 5.0 g of Na and 220 mL of EtOH) was added ethyl trifluoroacetoacetate (40.0 g, 0.217 mol). After 10 min, ethyl 3-bromopropionate (35.0 g, 0.194 mol) was added and the mixture was heated under reflux for 24 h. The reaction mixture was concentrated, taken up in ether, and washed with water. The ether layers were dried (MgSO4) and concentrated to give 50 g of a yellow oil. Distillation (100°-110° C./25 min) gave 14.0 g (23%) of product as a colorless oil.

Provenance & Evidence