3-Tert-butyldimethylsilyloxy-2,5-difluorobenzaldehyde → 1-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A 200 mL round bottom flask was charged with 90.B (1.38 g, 5.1 mmol) and THF (10 mL) and cooled to −78° C. under N2. To the cold solution was added ethylmagnesium bromide (3.0 M in ether) (commercially available from Aldrich) (5.1 mL, 15 mmol) dropwise. The mixture was stirred for 30 minutes at −78° C. The cooling bath was removed, and the mixture was stirred for 30 minutes at ambient temperature. The reaction was quenched with saturated aqueous ammonium chloride and diluted with EtOAc. The organic layers were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-15% EtOAc/hexane) to afford 90.C (0.48 g, 31% yield) as a colorless oil.

Provenance & Evidence