Reaction #2329017

Reaction equation

NaH

trans 2-allyloxy-cyclohexanol

4-fluoro-2-trifluoromethyl benzonitrile

→

product

Yield 26.2%

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

Yield 26.2%

Solvents

DMF

Conditions

Workup

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

Procedure

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.

Source