4-Toluenesulfonyl chloride → HCID 86683232, compound

Participants

Reaction Steps

To a solution of (2S)-4-methyloct-7-en-2-ol (39.0 g, 0.274 moles) in pyridine (400 mL) was added 4-(dimethylamino)pyridine (“DMAP”, 1.67 g, 0.013 moles) and the solution was stirred for 10 min. p-toluenesulfonyl chloride (60 g, 0.315 moles) was added to the reaction mass at 0° C. The reaction mass was allowed to come to room temperature and stirred overnight. Pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (200 mL). The organic solution was washed with aqueous 1.5 N HCl solution, saturated aq. Bicarbonate solution, brine solution, dried over anhydrous Na2SO4, filter, and concentrated under reduced pressure to get crude compound (2S)-4-methyloct-7-en-2-yl 4-methylbenzenesulfonate (54 g, 61%). The crude compound was taken to the next step without further purification.

Provenance & Evidence