Reacción #2329017

Ecuación de reacción

NaH

trans 2-allyloxy-cyclohexanol

4-fluoro-2-trifluoromethyl benzonitrile

→

product

Rendimiento 26.2%

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

Rendimiento 26.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente