2(3H)-Benzoxazolone → 3-(3-methyl-3-nitro-butyl)-3H-benzoxazol-2-one

Participants

Reaction Steps

1.70 g (42.5 mmol) sodium hydride (60%) are added batchwise to a solution of 4.50 g (33.3 mmol) benzoxazol-2-one in 50 mL DMF, while the temperature is kept below 0° C. by cooling. After one hour's stirring a solution of 9.61 g (37.4 mmol) 1-iodo-4-methyl-4-nitro-pentane in 20 mL DMF is added dropwise so that the temperature does not exceed 5° C. The mixture is stirred overnight at ambient temperature and the solvent is distilled off. The residue is taken up in ethyl acetate and washed successively with water and sodium chloride solution, dried with sodium sulphate and evaporated down. 11.0 g oil are obtained. Mass spectroscopy: [M+H]+=265.

Provenance & Evidence