Triethylamine → 2-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of 2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethanol (12.5 g, 61 mmol) in dichloromethane (200 mL) at −20° C. under N2 atmophere was added triethylamine (26 mL, 184 mmol) and catalytic amount of 4-dimethylamino pyridine (50 mg). This solution was then treated with toluenesulfonyl chloride (14.1 g, 73.8 mmol) and the reaction was allowed to equilibrate to 23° C. over 16 hours. Reaction was washed with water, 5% Na2CO3, saturated NH4Cl, and brine. Solvent was removed in vacuo and crude tosylate 1 (21.3 g) was carried on to the next step without further purification. M+1=358.2

Provenance & Evidence