4-Toluenesulfonyl chloride → 3-Azidopropyl 4-methylbenzenesulfonate

Participants

Reaction Steps

Acetic acid 3-azido-propyl ester (3.16 g, 22.1 mmol) was dissolved in water (25 mL) and methanol (25 mL). To the resulting mixture was then added potassium carbonate (3.81 g, 27.6 mmol) and the resulting solution was stirred for 2 hours at room temperature, reduced to a third of its volume, saturated with MgSO4, filtered and partitioned with water and dichloromethane. The organic layer was dried with magnesium sulfate, filtered and transferred into to dry round bottom flask. To the filtrate was then added (3.35 g, 33.1 mmol) and tosyl chloride (4.6 g, 24.3 mmol) and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was partitioned with aqueous 1N HCl and dichloromethane. The organic layer was dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (10% ethyl acetate/hexanes) to yield the toluene-4-sulfonic acid 3-azido-propyl ester (2.03 g) as an oil.

Provenance & Evidence