反应详情

温度

65 °C

A mixture of [4-(4-hydroxyphenyl)butyl]carbamic acid benzyl ester 1 (2.00 g, 6.70 mmol), 4-bromobutyronitrile (0.70 mL, 6.70 mmol), and potassium carbonate (1.00 g, 7.4 mmol) in DMF (10 mL), was stirred at 65° C. for 16 h. Solvent was removed by rotary evaporation and the residue was taken up in ethyl acetate, washed with water and brine, and concentrated under vacuum. The crude product was purified by flash silica gel column chromatography eluting with ethyl acetate/CH2Cl2 (1:9, v/v) to give the desired product 2 as a white solid (1.80 g, 75% yield). 1H NMR (300 MHz, CDCl3) δ 1.56 (m, 4H), 2.15 (m, 2H), 2.55 (m, 4H), 3.15 (m, 2H), 4.00 (m, 2H), 4.70 (br s, 1H), 5.10 (s, 2H), 6.80 (d, 2H), 7.05 (d, 2H), 7.30 (m, 5H). m/z (ESI): 367 [C22H26N2O3+H]+.

1. customSolvent was removed by rotary evaporation
2. washwashed with water and brine
3. concentrationconcentrated under vacuum
4. customThe crude product was purified by flash silica gel column chromatography
5. washeluting with ethyl acetate/CH2Cl2 (1:9, v/v)