Hydrochloric Acid → HCID 86731007, compound

Participants

Reaction Steps

To a solution of 2-(4-bromophenyl)-2-methylpropanal (5.7 g, 25 mmol) and trimethyl(trifluoromethyl)silane (7.1 g, 50 mmol) in THF (60 mL) under nitrogen was added a solution of TBAF (0.66 g, 2.5 mmol) in THF (10 mL) dropwise at −30° C. The resulting solution was stirred at −30° C. for 1 hour and at ambient temperature for an additional 1 hour before the addition of 1 N aqueous HCl (20 mL). The mixture was vigorously stirred at ambient temperature for 10 minutes, and then extracted with EtOAc (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 2-4% EtOAc/hexane) to afford (S and R)-3-(4-bromophenyl)-1,1,1-trifluoro-3-methylbutan-2-ol as a light yellow oil. The racemic mixture was resolved by preparative chiral HPLC (Chiralpak IA, 2*25 cm; Mobile phase: 5% ethanol in hexane) to afford the two enantiopure title compounds.

Provenance & Evidence