4-Toluenesulfonyl chloride → HCID 86672628, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 0.49 mL (3.5 mmol) of triethylamine, 0.68 g (3.54 mmol) of p-toluenesulfonyl chloride, and 15 mg (0.16 mmol) of trimethylamine hydrochloride were added to a solution of 1.0 g (3.2 mmol) of 4,8,12,16-tetramethylheptadec-3-en-1-ol in dry methylene chloride (3.2 mL) at 0° C., sequentially. After being stirred for 2 hours at room temperature, 0.080 mL (0.64 mmol) of N,N-dimethyl-1,3-propanediamine was added to the reaction mixture at 0° C. After being stirred for 15 min, water was added, and the mixture was extracted with methylene chloride. The extract was washed with 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain (4,8,12,16-tetramethylheptadec-3-enyl)tosylate as a crude product.

Provenance & Evidence