反应 #2329017

反应方程式

NaH

trans 2-allyloxy-cyclohexanol

4-fluoro-2-trifluoromethyl benzonitrile

→

product

收率 26.2%

(1S,2S)-4-(2-Allyloxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile

收率 26.2%

溶剂

DMF

反应条件

后处理

1. 1
   workup.STIRRINGthe solution was stirred at room temperature overnight
2. 2
   萃取The DMF solution was extracted twice with hexane
3. 3
   workup.ADDITIONThen the reaction mixture was poured into 100 mL of water
4. 4
   萃取extracted three times with ether
5. 5
   萃取The combined ether layers were extracted three times with water
6. 6
   干燥once with brine, and dried over magnesium sulfate
7. 7
   过滤filtered
8. 8
   其他the solvent removed
9. 9
   其他The crude product was chromatographed with a hexane/methylene chloride mixture (100% hexane to 1:1 hexane/methylene chloride)
10. 10
    其他the solvent removed

实验过程

To 15 mL anhydrous DMF (dimethylformamide) was added trans 2-allyloxy-cyclohexanol (1.144 g, 7.323 mmol), then NaH (60% in oil, 0.4261 g, 10.65 mmol) was added and stirred at room temperature 15 min. Then 4-fluoro-2-trifluoromethyl benzonitrile (1.435 g, 7.59 mmol) was added, and the solution was stirred at room temperature overnight. The DMF solution was extracted twice with hexane. Then the reaction mixture was poured into 100 mL of water and extracted three times with ether. The combined ether layers were extracted three times with water, then once with brine, and dried over magnesium sulfate, filtered, and the solvent removed. The crude product was chromatographed with a hexane/methylene chloride mixture (100% hexane to 1:1 hexane/methylene chloride). The desired fractions were combined, and the solvent removed to give 0.6245 g product. HNMR (CDCl3, ppm) 7.70-7.68 (1H, d, J=8.8 Hz), 7.32 (1H, s), 7.19-7.16 (1H, d, J=8.8 Hz), 5.80-5.71 (1H, m), 5.20-5.0 (2H, m), 4.30-4.20 (1H, m), 4.10-4.00 (1H, m) 4.00-3.90 (1H, m), 3.50-3.39 (1H, m), 2.20-2.00 (2H, m), 1.80-1.70 (2H, m), 1.65-1.20 (5H, m). FNMR (CDCl3)-62.67 ppm. MS+326.

来源