Acetone → HCID 11502536, compound

Participants

Reaction Steps

(5-Bromo-2-hydroxyphenyl)-(1-phenyl-1H-pyrazol-4-yl)ketone (100 mg, 0.29 mmol), (R)-(+)-bromoacetic acid (44 mg, 0.29 mmol) ethyl 2-bromopropionate and K2CO3 (80 mg, 0.58 mmol) in acetone was stirred at room temperature for 16 h. The reaction mixture was concentrated and the residue was partitioned between EtOAc and dilute HCl (pH˜1). The organic phase was dried (Na2SO4) and concentrated, and the residue was purified by flash chromatography (EtOAc:heptane, 1:1) to yield 55 mg (46%) of the title compound: Chiral HPLC (Column: Ciracel OD (0.46 cm×24 cm); Eluent: isocratic, 85% hexane+15% 2-propanol+0.1% TFA; Flow 0.5 mL/min) Rt 15.7 min, >90% e.e. (Racemic material eluates with baseline separation of enantiomers: Rt 15.7 and 16.7 min.) MS and NMR spectra correspond to racemic material.

Provenance & Evidence