Methyl chloroformate → HCID 71227062, compound

Participants

Reaction Steps

Methyl chloroformate (1.67 mL, 21.54 mmol) was slowly added to a 0° C. solution of 3-(oxazol-5-yl)aniline (2.30 gm, 14.36 mmol) and TEA (4.00 mL, 28.70 mmol) in THF (65 mL). The ice bath was removed and the reaction mixture was stirred at rt. After 2.5 h the reaction mixture was concentrated and the residue was partitioned between EtOAc and water. The organic phase was isolated, washed with 1 N HCl (2×) and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes to give the product, methyl 3-(oxazol-5-yl)phenylcarbamate, (1.34 gm, 6.14 mmol, 43% yield) as a white solid. Anal. Calcd. for C11H10N2O3 m/z 218.1, found: 219.1 (M+H)+.

Provenance & Evidence