Tetrabutylammonium Fluoride → 2-Fluoro-5-[(4-hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile
反応式
[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]参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
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).