Chlorotrimethylsilane → HCID 58292869, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of powdered zinc dust (3.3 g, 51 mmol) in THF (20 mL) was added trimethylsilyl chloride at room temperature. The reaction mixture was stirred at 40° C. for 20 min and ethyl bromoacetate (5.59 g, 33.0 mmol) was slowly added, the reaction mixture was stirred at 40° C. for an additional 30 min. To a solution of 2-(benzyloxy)-4-(tetrahydro-2H-pyran-2-yloxy)-6-(3,3,4,4-tetramethylborol-1-yl)benzaldehyde (2.8 g, 6.4 mmol) in THF (15 mL) was added dropwise the above prepared zinc reagent at −78° C. The reaction mixture was stirred at room temperature for 1 h and quenched by saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a light yellow oil (1.3 g, yield: 48%).

Provenance & Evidence