反应详情

A solution of TosMIC (15.7 g, 80.5 mmol) and 5 (14.6 g, 76.7 mmol) in a dry ether/DMSO (2:1) (154 mL) solution was added dropwise under argon to a stirred solution of NaH (2.39 g, 99.7 mmol) in ether (70 mL). The mixture started to reflux due to the exothermic reaction. After 3 h, water (200 mL) was carefully added to the mixture and the aqueous phase was extracted with ether and CH2Cl2. The combined organic extracts were dried (Na2SO4), concentrated, and chromatographed [silica, CH2Cl2/ethyl acetate (9:1)] to give a light brown solid (13.1 g, 74%): mp 154-155° C.; 1H NMR δ 1.25 (t, J=7.2 Hz, 3H), 2.36 (s, 3H), 4.22 (q, J=7.2 Hz, 2H), 6.75-6.77 (m, 1H), 7.16 (d, J=7.8 Hz, 2H), 7.38 (d, J=7.8 Hz, 2H), 7.46-7.48 (m, 1H), 8.38-8.54 (br, 1H); 13C NMR δ 14.5, 21.4, 59.8, 113.9, 118.3, 125.4, 126.8, 128.6, 129.4, 132.0, 136.3, 165.2; Anal. Calcd for C14H15NO2: C, 73.34; H, 6.59; N, 6.11. Found: C, 73.11; H, 6.59; N, 6.12.

1. temperatureto reflux due to the exothermic reaction
2. extractionthe aqueous phase was extracted with ether and CH2Cl2
3. dry with materialThe combined organic extracts were dried (Na2SO4)
4. concentrationconcentrated
5. customchromatographed [silica, CH2Cl2/ethyl acetate (9:1)]