Imidazole → 2-(6-t-Butyldimethylsilyloxyhexylthio)-4-t-butyldimethylsilyloxy-2-cyclopentenone

HRID 358374Notes

Reaction equation

HRID 358374 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9]1[C:10](=[O:22])[CH2:11][CH:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH:13]=1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CN=C1>CN(C)C=O>[Si:23]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9]1[C:10](=[O:22])[CH2:11][CH:12]([O:14][Si:15]([C:18]([CH3:19])([CH3:21])[CH3:20])([CH3:16])[CH3:17])[CH:13]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 20448815HCID 20448815, compound

Product 1

HCID 204488392-(6-t-Butyldimethylsilyloxyhexylthio)-4-t-butyldimethylsilyloxy-2-cyclopentenoneYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

440 mg (1.28 mmoles) of 2-(6-hydroxyhexylthio)-4-t-butyldimethylsilyloxy-2-cyclopentenone and 225 mg (1.50 mmoles) of t-butyldimethylsilyl chloride were treated at room temperature for 2 hours in 3 ml of N,N-dimethyl formamide in the presence of 204 mg (3.0 mmoles) of imidazole. After the reaction, the reaction mixture was extracted with hexane to give 640 mg of a crude product. The crude product was purified by thin-layer chromatography (cyclohexane/ethyl acetate=4/6) to give 437 mg (75%) of 2-(6-t-butyldimethylsilyloxyhexylthio)-4-t-butyldimethylsilyloxy-2-cyclopentenone.

Workup

  1. customAfter the reaction
  2. extractionthe reaction mixture was extracted with hexane
  3. customto give 640 mg of a crude product
  4. customThe crude product was purified by thin-layer chromatography (cyclohexane/ethyl acetate=4/6)

Sources & evidence

ORD record
ord-40b47ccb138d4834835fbd07d910bee0
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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