反応 #2329016

反応方程式

Cyclohexene oxide

4-fluoro-2-(trifluoromethyl)benzonitrile

potassium carbonate

water

→

4-(2-hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile

収率 50.0%

溶媒

DMF

反応条件

後処理

1. 1
   温度to cool
2. 2
   抽出extracted with ethyl acetate (200 mL) three times
3. 3
   洗浄The combined extracts were washed with water (300 mL), 0.5M NaOH (300 mL), water (300 mL)
4. 4
   乾燥The organic phase was dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他The crude material was purified by chromatography on silica
8. 8
   洗浄eluting with a 2:1 solution of hexane

実験手順

Cyclohexene oxide (13.11 g, 133.6 mmol), 4-fluoro-2-(trifluoromethyl)benzonitrile (5.00 g, 26.72 mmol), and potassium carbonate (5.539 g, 40.08 mmol) in DMF (dimethylformamide) (50 mL) were heated to 95° C. for 14 hours. The reaction was then allowed to cool. The reaction was added to water (300 mL) and then extracted with ethyl acetate (200 mL) three times. The combined extracts were washed with water (300 mL), 0.5M NaOH (300 mL), water (300 mL), and a 15% sodium chloride solution (300 mL). The organic phase was dried over sodium sulfate, filtered and evaporated. The crude material was purified by chromatography on silica, eluting with a 2:1 solution of hexane:ethyl acetate. This yielded the desired product, 4-(2-hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile (3.8 g, 50% yield).

出典