Sodium hydride → HCID 59203857, compound

HRID 2241835Notes

Reaction equation

HRID 2241835 reaction equation
[CH2:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[OH:11])[CH:2]=[CH2:3].[H-].[Na+].F[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=1>CN(C)C=O>[CH2:1]([O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[O:11][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:24])([F:26])[F:25])[CH:16]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 10080611HCID 10080611, compound

Product 1

HCID 59203857HCID 59203857, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. stirringthe solution was stirred at room temperature overnight
  2. extractionThe DMF solution was extracted twice with hexane
  3. additionThen the reaction mixture was poured into 100 mL of water
  4. extractionextracted three times with ether
  5. extractionThe combined ether layers were extracted three times with water
  6. dry with materialonce with brine, and dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed
  9. customThe crude product was chromatographed with a hexane/methylene chloride mixture (100% hexane to 1:1 hexane/methylene chloride)
  10. customthe solvent removed

Sources & evidence

ORD record
ord-42f598d875ef4e0cb9f30e42b75c7877
Source dataset
uspto-grants-2010_03
Patent number
US07670613B2

Reaction notes

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