Imidazole → 4-[4-(t-Butyldimethylsilyl)oxy-2,6,6-trimethylcyclohex-1-enyl]but-3-en-2-one

HRID 703620Notes

Reaction equation

HRID 703620 reaction equation
CN(C)C=O.N1C=CN=C1.[OH:11][CH:12]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]([CH:20]=[CH:21][C:22](=[O:24])[CH3:23])=[C:14]([CH3:25])[CH2:13]1.[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27]>C(OCC)C>[Si:30]([O:11][CH:12]1[CH2:17][C:16]([CH3:18])([CH3:19])[C:15]([CH:20]=[CH:21][C:22](=[O:24])[CH3:23])=[C:14]([CH3:25])[CH2:13]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 5389533-Buten-2-one, 4-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E)-

Product 1

HCID 541718584-[4-(t-Butyldimethylsilyl)oxy-2,6,6-trimethylcyclohex-1-enyl]but-3-en-2-oneYield 80.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 30 ml of an anhydrous dimethylformamide (hereinafter "DMF") solution containing 588 mg of imidazole and 1.2 g of 4-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one was added dropwise 15 ml of an anhydrous DMF solution containing 1.3 g of t-butyldimethylchlorosilane at room temperature in a nitrogen atmosphere. After the dropwise addition, the mixture was stirred under the same conditions for 15 hours. Diethyl ether was added to the reaction mixture, and the mixture was washed several times with water cooled with ice. The organic layer was dried over anhydrous magnesium sulfate, and the solvent, etc. were removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.5 g (yield: 78%) of 4-[4-(t-butyldimethylsilyl)oxy-2,6,6-trimethylcyclohex-1-enyl]-but-3-en-2-one.

Workup

  1. additionAfter the dropwise addition
  2. washthe mixture was washed several times with water
  3. temperaturecooled with ice
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent, etc. were removed by distillation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d61367c28e8e430e8cb76c4270bde4b0
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

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