Reaktion #992714

Reaktionsgleichung

imidazole

9n

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

TIPSCl

→

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

Ausbeute 96.0%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Sonstigethe solvents were removed under reduced pressure
3. 3
   SonstigeThe residue was purified by flash column chromatography
4. 4
   Wascheneluted by hexane:ethyl acetate (6:1)
5. 5
   Sonstigethe correct product was obtained as a slightly yellow oil

Vorschrift

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.

Quelle