Dichloromethane → 3-Butynyl p-toluenesulfonate

Participants

Reaction Steps

Triethylamine (12.2 mL) was added dropwise to a mixture of 3-butyn-1-ol (5.09 g) and 4-toluenesulfonyl chloride (16.95 g) in 50 nm of CH2Cl2 cooled by an ice bath. The mixture was allowed to warm to room temperature. After 21 hours, the mixture was poured into ethyl acetate (150 mL) and washed with 0.1M HCl (75 mL), saturated NaHCO3 (75 mL), and brine (75 mL) and the organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. Purification by flash chromatography (10% ethyl acetate/hexane) gave 16.57 g of the product as a colorless solid.

Provenance & Evidence