Imidazole → HCID 15728608, compound

HRID 1197052Notes

Reaction equation

HRID 1197052 reaction equation
[CH3:1][S:2][C:3]1[C:4](=[O:20])[CH2:5][C:6]([OH:19])([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1.N1C=CN=C1.Cl[Si:27]([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[CH3:1][S:2][C:3]1[C:4](=[O:20])[CH2:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([O:19][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 15728609HCID 15728609, compound

Product 1

HCID 15728608HCID 15728608, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 400 mg of 2-methylthio-4-hydroxy-4-(4-phenoxybutyl)-2-cyclopentenone obtained in Example 52 or Example 53 dissolved in 4 ml of dimethylformamide were added 279 mg of imidazole and 260 μl of chlorotrimethylsilane, under ice-cooling and stirring, and the mixture was stirred at 0° C. for 3 hours. The reaction mixture was extracted with an addition of water and hexane. The organic layer was washed with saturated aqueous sodium chloride, and the product dried over anhydrous sodium sulfate, filtered and concentrated, followed by silica gel column chromatography, to give 445 mg (yield 89%) of 2-methylthio-4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at 0° C. for 3 hours
  3. extractionThe reaction mixture was extracted with an addition of water and hexane
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialthe product dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3054ea54cc43418d81b48a6d551d178f
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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