Imidazole → 1-Acetoxy-8-(dimethyl t-butylsilyl)oxy-3,7-dimethyl-2,6-octadiene

HRID 5654Notes

Reaction equation

HRID 5654 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:14])[CH2:12][OH:13])(=[O:3])[CH3:2].N1C=CN=C1.Cl[Si:22]([CH3:28])([CH3:27])[C:23]([CH3:26])([CH3:25])[CH3:24].O>CN(C)C=O>[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:14])[CH2:12][O:13][Si:22]([CH3:28])([CH3:27])[C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 539043298-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol

Product 1

HCID 539786501-Acetoxy-8-(dimethyl t-butylsilyl)oxy-3,7-dimethyl-2,6-octadieneYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol in dimethylformamide (4 ml) was stirred on an ice bath. To the solution were added imidazole (338 mg, 4.96 mmol) and chlorodimethyl t-butylsilane (410 mg, 2.73 mmol), and the mixture was stirred at room temperature for one hour. After addition of water (30 ml) to the reaction mixture, the product was extracted with hexane (20 m1×2). The extract was dried over MgSO4 and evaporated in vacuo to remove the solvent to give a residue, which was subjected to silica gel column chromatography to obtain 1-acetoxy-8-(dimethyl t-butylsilyl)oxy-3,7-dimethyl-2,6-octadiene (606 mg, 75%).

Workup

  1. extractionthe product was extracted with hexane (20 m1×2)
  2. dry with materialThe extract was dried over MgSO4
  3. customevaporated in vacuo
  4. customto remove the solvent
  5. customto give a residue, which

Sources & evidence

ORD record
ord-80a36a4efaf343448d7ae9f9feb6eb02
Source dataset
uspto-grants-1993_09
Patent number
US05245085

Reaction notes

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