Imidazole → HCID 15728608, compound

HRID 1587130Notes

Reaction equation

HRID 1587130 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 551 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-e74c71274571411db2cf99f4f50c3059
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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