Trimethylsilyl triflate → HCID 16083429, compound

Participants

Reaction Conditions

Reaction Steps

1.5 g of (4,4-Dimethoxy-cyclohexyloxymethyl)-benzene (38) were dissolved in 20 mL of dry dichloromethane and cooled to 0° C. 3.05 mL of trimethylsilyl cyanide were added dropwise and after stirring for 2 minutes, 1.31 mL of trimethylsilyl trifluoromethansulfonate were added dropwise. The mixture was stirred at 0° C. for 2 h, then 20 mL of saturated aqueous sodium bicarbonate solution were added dropwise. Phases were separated and the aqueous layer was extracted several times with dichloromethane. The combined organic layer was dried and evaporated to dryness to give 1.5 g of crude product, that was purified by silica gel chromatography to give 1.3 g of the desired compound as a cis-trans-mixture. Rt=4.68 min (Method D). Detected mass: 246.1 (M+H+).

Provenance & Evidence