Chlorotrimethylsilane → HCID 86721096, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of zinc (0.848 g, 12.98 mmol) in dry THF (10 mL), was added chlorotrimethylsilane (0.829 mL, 6.49 mmol). After 10 min, tert-butyl 2-bromoacetate (0.959 mL, 6.49 mmol) was added and the reaction mixture was heated at 50° C. for 10 min. The reaction mixture was then cooled to 0° C. under argon. To the cooled solution was then added 2-fluoro-3-methoxybenzaldehyde (1 g, 6.49 mmol) in THF (3 mL) and the reaction was allowed to warm to rt overnight. The reaction mixture after overnight stirring was quenched with 5% NaHCO3 solution, filtered off the solids and rinsed with EtOAc. The organic layer was washed with water followed by brine and dried over MgSO4 to yield the crude product. The crude product was then purified using silica gel chromatography to yield the desired product (1.02 g, 58%) as clear oil. MS (ESI) m/z: 215.1 (M-tBu)+.

Provenance & Evidence