4-Toluenesulfonyl chloride → (1-(Hydroxymethyl)cyclopent-3-en-1-yl)methyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of cyclopent-3-ene-1,1-diyldimethanol (44.0 g, 343 mmol), triethylamine (34.7 g, 343 mmol) and 4-dimethylaminopyridine (4.19 g, 34.3 mmol) in dichloromethane (2 L) was added tosyl chloride (58.9 g, 309 mmol) portionwise. The reaction mixture was warmed to 26° C. After 16 h, the mixture was concentrated, and the resulting residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether)) to afford product as a brown solid (34 g, 35% yield).

Provenance & Evidence