4-Toluenesulfonyl chloride → 2-(1-methyl-1H-pyrrol-2-yl)ethyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a stirred and cooled (±5° C.) mixture of 20.7 parts of 1-methyl-1H-pyrrole-2-ethanol and 200 parts of dry pyridine are added portionwise 35.9 parts of 4-methylbenzenesulfonyl chloride. Upon completion, stirring is continued for 6 hours at about 5° C. The reaction mixture is allowed to stand overnight at 0° C. and poured onto water. The product is extracted with benzene. The extract is washed successively with a 20% hydrochloric acid solution, water, a 10% sodium carbonate solution and with water, dried, filtered and evaporated, yielding 33.4 parts (76.8%) of 2-(1-methyl-1H-pyrrol-2-yl)ethyl 4-methylbenzenesulfonate as an oily residue.

Provenance & Evidence