HRID877401

反应详情

EQUATION

反应方程式

HRID 877401 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

4-Biphenylethanol (see Kawasaki et al., Tetrahedron: Asymmetry 2001, 12, 585-596) (1.47 g, 7.41 mmol) and CBr4 (1.12 equiv) were dissolved in CH2Cl2 (25 mL), the mixture was cooled to 0° C. and triphenylphosphine (1.1 equiv) was added in small portions. The reaction mixture was warmed at room temperature and stirred for 1 h before the solvent was removed in vacuo. Flash chromatography (0-5% EtOAc-hexanes) yielded 4-(2-bromoethyl)biphenyl (1.59 g, 82%). The title compound was prepared from S7 (55 mg, 0.27 mmol) and 4-(2-bromoethyl)biphenyl (280 mg, 1.07 mmol) by using general procedure D. Flash chromatography (SiO2, 1.5×18 cm, 50-100% EtOAc-hexanes) afforded the title compound (38 mg, 40%) as a white solid: 1H NMR (CDCl3, 500 MHz) δ 8.84 (dd, 1H, J=0.7, 4.7 Hz), 8.29 (d, 1H, J=7.9 Hz), 7.92 (dt, 1H, J=1.7, 7.8 Hz), 7.57 (m, 2H), 7.53 (m, 3H), 7.42 (t, 2H, J=7.7 Hz), 7.33 (m, 3H), 3.60 (t, 2H, J=7.5 Hz), 3.19 (t, 2H, J=7.5 Hz); 13C NMR (CDCl3, 150 MHz) δ 186.2, 165.3, 161.3, 150.9, 142.7, 141.0, 139.6, 139.0, 137.5, 129.0, 128.9, 127.5, 127.3, 127.2, 126.9, 124.2, 41.7, 29.1; HRMS-ESI-TOF m/z 356.1392 ([M+H]+, C22H17N3O2 requires 356.1393).

WORKUP

后处理

  1. temperatureThe reaction mixture was warmed at room temperature
  2. customwas removed in vacuo