Imidazole → 4-(4-(Tert-butyldimethylsilyloxy)phenyl)-4-(2-fluorophenyl)cyclohexanone

HRID 2174434Notes

Reaction equation

HRID 2174434 reaction equation
N1C=CN=C1.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1.[CH3:27][C:28]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])[CH3:29].C([O-])(O)=O.[Na+]>CN(C=O)C>[Si:31]([O:26][C:23]1[CH:22]=[CH:21][C:20]([C:13]2([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[F:6])[CH2:14][CH2:15][C:16](=[O:19])[CH2:17][CH2:18]2)=[CH:25][CH:24]=1)([C:28]([CH3:30])([CH3:29])[CH3:27])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 712451354-(2-Fluorophenyl)-4-(4-hydroxyphenyl)cyclohexanone

Product 1

HCID 712451054-(4-(Tert-butyldimethylsilyloxy)phenyl)-4-(2-fluorophenyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (128 mg, 1.9 mmol) was added to a solution of 6 (214 mg, 0.75 mmol) and TBDMSCl (136 mg, 0.90 mmol) in DMF (8 mL). The mixture was stirred at room temperature overnight. NaHCO3 (10 mL, saturated aqueous solution) was added and the mixture was extracted with EtOAc (2×40 mL). The combined organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure. The concentrate was dissolved in EtOAc (50 mL) and the solution was washed with MgSO4 (4% aqueous solution). The organic phase was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. Yield of crude: 394 mg (>100%) as a thick oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×40 mL)
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe concentrate was dissolved in EtOAc (50 mL)
  5. washthe solution was washed with MgSO4 (4% aqueous solution)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-be7b3c33f41046fc9b1d88f06d467e4e
Source dataset
uspto-grants-2015_06
Patent number
US09061981B2

Reaction notes

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