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

HRID 2174434ノート

反応式

HRID 2174434 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-be7b3c33f41046fc9b1d88f06d467e4e
出典データセット
uspto-grants-2015_06
特許番号
US09061981B2

反応ノート

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