Tetrabutylammonium Fluoride → 2-Fluoro-5-[(4-hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile
반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([SiH2][O:24][C:25](C)(C)[C:26]1[CH:31]=[CH:30][C:29]([CH:32]([O:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][O:44]2)[C:33]2[CH:34]=[CH:35][C:36]([F:41])=[C:37]([CH:40]=2)[C:38]#[N:39])=[CH:28][CH:27]=1)(C)(C)C>ClCCl>[F:41][C:36]1[CH:35]=[CH:34][C:33]([CH:32]([C:29]2[CH:28]=[CH:27][C:26]([CH2:25][OH:24])=[CH:31][CH:30]=2)[O:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][O:44]2)=[CH:40][C:37]=1[C:38]#[N:39]참가 물질
4
반응물 2
생성물 1
시약·촉매·용매 1
실험 절차
Add tetrabutylammonium fluoride (1.0M in tetrahydrofuran, 5.27 mL, 5.27 mmol) to 5-[[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-2-fluoro-benzonitrile (1.20 g, 2.64 mmol) and stir the solution overnight. Dilute with dichloromethane and wash with water and brine. Dry the organic layer and concentrate the solution to afford the title compound (0.890 g, 2.60 mmol, 99%, mixture of diastereomers): 1H NMR (400 MHz, CDCl3) δ 1.55 (m, 2H), 1.68 (m, 2H), 1.74 (m, 2H), 3.46 (m, 1H), 3.77 (m, 1H), 4.60 (m, 1H), 4.67 (s, 2H), 5.78 (s, 1H), 7.10 (m, 1H), 7.27 (m, 4H), 7.55 (m, 1H), 7.64 (m, 1H).