2,6-Lutidine → HCID 58380992, compound

Participants

Reaction Conditions

Reaction Steps

6.4 g (51.1 mmol) of 4-hydroxy-cyclohexanecarbonitrile (121) were dissolved in 120 mL of dichloromethane, cooled to 0° C. and 14.9 mL (13.7 g, 128 mmol) of 2,6-lutidine and 15.4 mL (14.9 g, 56.2 mmol) of tert-butyldimethylsilyltrifluoromethanesulfonate were added. The reaction mixture was stirred for 16 h at room temperature, then additional 5.0 mL of tert-butyldimethylsilyltrifluoromethanesulfonate were added and stirring continued for 1 h. The reaction mixture was diluted with 100 mL of dichloromethane and washed with 100 mL of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine. The organic phase was dried over magnesium sulphate, filtered, concentrated in vacuo and purified by silica gel chromatography (heptanes:ethyl acetate) to give 9.76 g of the desired product. Rt=0.95 min (Method 18). Detected mass: 240.1 (M+H+).

Provenance & Evidence