反应 #992714

反应方程式

imidazole

9n

1-(2,4-Difluoro-phenyl)-2-(3-hydroxy-phenylsulfanyl)-ethanone

TIPSCl

→

1-(2,4-Difluoro-phenyl)-2-(3-triisopropylsilanyloxy-phenylsulfanyl)-ethanone

收率 96.0%

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   过滤The mixture was filtered
2. 2
   其他the solvents were removed under reduced pressure
3. 3
   其他The residue was purified by flash column chromatography
4. 4
   洗涤eluted by hexane:ethyl acetate (6:1)
5. 5
   其他the correct product was obtained as a slightly yellow oil

实验过程

To a 100 mL three-neck round bottom flask was added 9n (1.4 g, 5 mmol) and TIPSCl (1.15 g, 6 mmol) in CH2Cl2 (40 mL) under nitrogen at room temperature. Then a solution of imidazole (816 mg, 12 mmol) in CH2Cl2 (20 mL) was added dropwise. The resulting mixture was stirred for 24 h. The mixture was filtered and the solvents were removed under reduced pressure. The residue was purified by flash column chromatography eluted by hexane:ethyl acetate (6:1) and the correct product was obtained as a slightly yellow oil; yield 96% (2.1 g); H NMR (400 MHz, CDCl3): d 1.13 (m, 18H, 6×CH3), 1.29 (m, 3H, CH), 4.26 (s, 2H, SCH2), 6.75 (m, 1H, Ar), 6.89-6.97 (m, 4H, Ar), 7.15 (m, 1H, Ar), 7.95 (m, 1H, Ar); CNMR (100 MHz, CDCl3): δ 21.6, 17.7, 29.3, 104.3, 111.5, 118.5, 119.2, 121.5, 122.7, 129.5, 131.4, 135.9, 153.6, 156.3, 159.5, 162.3, 164.9; IR ν (cm−1) 2944, 2983, 2866, 1682, 1610, 1584, 1475, 1423, 1266, 1245, 1186, 1145, 1095, 997, 970, 943, 881, 852, 776, 683; ESI HRMS m/z calcd for C23H31F2O3SSi (M+OH)+ 453.17258, found 453.17226.

来源