反応 #2329017

反応方程式

NaH

trans 2-allyloxy-cyclohexanol

4-fluoro-2-trifluoromethyl benzonitrile

→

product

収率 26.2%

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

収率 26.2%

溶媒

DMF

反応条件

後処理

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

実験手順

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.

出典