Ethyl trifluoroacetate → 4,4,4-Trifluoro-1-[2-(trifluoromethyl)phenyl]butane-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2′-trifluoromethyl-acetophenone (225 mL, 15.0 mmol) in THF (20 mL, anhyd) at −78° C. added dropwise a 1.0M solution of lithium hexamethyldisilazide (LiHMDS) (15.8 mL, 15.8 mmol). After 1 h the reaction mixture was cooled to −78° C. and charged dropwise with ethyl trifluoroacetate (3.6 mL, 30 mmol). After addition was complete, the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was quenched by slow addition of H2O (20 mL) and concentrated under reduced pressure. The resulting material was transferred to a separatory funnel, diluted with Et2O (60 mL), washed with 1N HCl and brine, then dried (MgSO4) and concentrated to yield the title compound (4.2 g, 99%) as an amber liquid, which was used in the next step without purification. Rf: 0.15 (20% EtOAc/Hex).

Provenance & Evidence