2-Chloro-4-fluorobenzonitrile → HCID 17986305、化合物

反応式

CC(C)([O-])C.[K+].[OH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[Cl:21][C:22]1[CH:29]=[C:28](F)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>C(COC)OC>[Cl:21][C:22]1[CH:29]=[C:28]([CH:27]=[CH:26][C:23]=1[C:24]#[N:25])[O:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]1

参加物

実験手順

Potassium tert-butoxide (5.57 g, 49.68 mmol) was added to a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (5.00 g, 24.84 mmol) in glyme (100 ml) and the mixture stirred for 30 min. before addition of 2 chloro-4-fluoro-benzonitrile (7.73 g, 49.68 mmol). The reaction was stirred at room temperature overnight and then partitioned between ethyl acetate (250 ml) and water (200 ml). The organic layer was separated, dried over magnesium sulfate and the solvent evaporated. The residue was purified by flash chromatography eluting with ethyl acetate:isohexane (4:1) to give the subtitle compound as a colourless solid (3.45 g).