反应详情

To a stirred solution of butyryl chloride (0.770 g, 7.23 mmol) in chloroform ( 15 mL) was added N-methyl-4-nitroaniline and triethylamine (1.2 mL, 8.6 mmol). After overnight stirring, additional butyryl chloride (0.40 mL, 3.9 mmol) was added and the reaction was refluxed for 2-3 hours. The reaction was concentrated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was combined with a second ethyl acetate extract, dried (sodium sulfate) and concentrated. The resulting dirty yellow oil was purified by flash chromatography over silica (methylene chloride/methanol) to afford 1.11 g (76%) of product as a pale yellow solid: 1H NMR (CDCl3) δ 8.30 (d, J=8.9 Hz, 1H), 7.40 (d, J=8.9 Hz, 1H), 3.34 (s, 3H), 2.18 (t, J=7.5 Hz, 2H), 1.71-1.59 (m, 2H), 0.88 (t, J=7.6Hz,

1. temperaturethe reaction was refluxed for 2-3 hours
2. concentrationThe reaction was concentrated
3. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
4. extractionextract
5. dry with materialdried (sodium sulfate)
6. concentrationconcentrated
7. customThe resulting dirty yellow oil was purified by flash chromatography over silica (methylene chloride/methanol)