反应详情

Acetylchloride (0.7 g, 8.9 mmol) is slowly added to a cooled (0° C.) mixture of 2-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (3.0 g, 8.0 mmol) and pyridine (0.7 g, 8.9 mmol) in 30 ml of dichloromethane. The reaction mixture is stirred for 2 hours at room temperature and subsequently poured on ice and extracted with ethyl acetate. The combined organic extracts are washed with brine, dried over sodium sulfate and the solvent is evaporated, the residue is purified by chromatography on silica gel to give 2-acetoxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide. 1H-NMR (300 MHz, CDCl3): 2.13 (s, 3H, CH3CO2), 2.52 (t, 1H, C≡CH), 2.80 (t, 2H, CH2CH2), 3.57 (t, 2H, CH2CH2), 3.87 (s, 3H, OCH3), 4.79 (d, 2H, OCH2C≡C), 6.03 (s, 1H, CHOH), 6.65–7.34 (m, 8H, CH arom., NH).

1. temperaturea cooled
2. additionsubsequently poured on ice
3. extractionextracted with ethyl acetate
4. washThe combined organic extracts are washed with brine
5. dry with materialdried over sodium sulfate
6. customthe solvent is evaporated
7. customthe residue is purified by chromatography on silica gel