Cyclohexanol → HCID 17605576, compound

HRID 2241913Notes

Reaction equation

HRID 2241913 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=1[C:20]([F:23])([F:22])[F:21]>O1CCCC1>[CH:1]1([O:7][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[C:20]([F:21])([F:23])[F:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 949542-Fluoro-5-nitrobenzotrifluoride

Product 1

HCID 17605576HCID 17605576, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cyclohexanol (1.00 g, 10.0 mmol) in anhydrous tetrahydrofuran (6 ml) was added dropwise to a suspension of 60% sodium hydride (0.240 g, 6.00 mmol) in anhydrous tetrahydrofuran (6 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour. 1-Fluoro-4-nitro-2-(trifluoromethyl)benzene (1.05 g, 5.00 mmol) was added to the reaction mixture under ice cooling, and the mixture was refluxed for 3 hours. Ice water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Methanol (10 ml) and 10% platinum on activated carbon (0.100 g) were added to the residue obtained by evaporation of the solvent under reduced pressure, and the mixture was stirred at room temperature for 12 hours under hydrogen atmosphere. The reaction mixture was filtered through celite. The residue obtained by concentration of the filtrate under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (0.60 g, 47%) as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. additionMethanol (10 ml) and 10% platinum on activated carbon (0.100 g) were added to the residue
  6. customobtained by evaporation of the solvent under reduced pressure
  7. stirringthe mixture was stirred at room temperature for 12 hours under hydrogen atmosphere
  8. filtrationThe reaction mixture was filtered through celite
  9. customThe residue obtained by concentration of the filtrate under reduced pressure
  10. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-dc7134ec66ad469d812f0083e0937948
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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