Dimethylformamide → 3-Tert-butyldimethylsilyloxy-2,5-difluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A 500 mL round bottom flask was charged with 90.A (8.60 g, 35.2 mmol) and THF (70 mL) and cooled to −78° C. under N2. To the cold solution was added sec-butyllithium (1.4 M in cyclohexane) (available from Aldrich) (27.7 mL, 38.7 mmol) dropwise. The mixture was stirred for 30 minutes, and to it was added DMF (4.09 mL, 52.8 mmol) dropwise. The mixture was stirred for 30 minutes at −78° C., warmed to room temperature over 30 minutes, quenched with 1 N HCl, 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 (0-5% EtOAc/hexane) to afford 90.B (5.71 g, 59.6% yield) as a colorless oil.

Provenance & Evidence