Chlorotrimethylsilane → HCID 58292634, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of zinc powder (0.65 g, 10.0 mmol) in anhydrous THF (15 mL) was added TMSCl (0.13 mL, 1.0 mmol) at 40° C. The resulting mixture was stirred at 55° C. for 15 min and cooled to 37° C., followed by addition of ethyl 2-bromoacetate (0.45 mL, 4.0 mmol). The reaction mixture was stirred at this temperature for an additional 30 min. To the solution of 2,4-dimethoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde (0.29 g, 1.0 mmol) in anhydrous THF (20 mL) cooled at −78° C., was added above prepared solution dropwise. The reaction mixture was allowed to stir at room temperature for 1.5 hr and quenched by aqueous ammonium chloride (20 mL). The reaction mixture was extracted with ethyl acetate (2×15 mL), the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/3) on silica gel to give the title compound as a white solid. (110 mg, Yield: 39.3%). MS (ESI) m/z=281 [M+H]+.

Provenance & Evidence