Imidazole → 4-Trimethylsiloxy-4-vinyl-1-iodo-trans-1-octene

HRID 1701411Notes

Reaction equation

HRID 1701411 reaction equation
[OH:1][C:2]([CH:11]=[CH2:12])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3]/[CH:4]=[CH:5]/[I:6].N1C=CN=C1.Cl[Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O>[CH3:20][Si:19]([CH3:22])([CH3:21])[O:1][C:2]([CH:11]=[CH2:12])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3]/[CH:4]=[CH:5]/[I:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 128512814-Hydroxy-4-vinyl-1-iodo-trans-1-octene

Product 1

HCID 128512834-Trimethylsiloxy-4-vinyl-1-iodo-trans-1-octene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 456 mg of 4-hydroxy-4-vinyl-1-iodo-trans-1-octene and 320 mg of imidazole in 1.0 ml of dimethylformamide is added 0.23 ml of chlorotrimethylsilane during 3 minutes. The mixture is stirred at room temperature for 22 hours and partitioned with a mixture of cold hexane and water. The hexane layer is washed repeatedly with water and then brine, dried over magnesium sulfate, and concentrated to give an oil, pmr spectrum (CDCl3): 0.13 (s, trimethylsiloxy group) and 2.32 (d, =CHCH2).

Workup

  1. custompartitioned with a mixture of cold hexane and water
  2. washThe hexane layer is washed repeatedly with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil, pmr spectrum (CDCl3)

Sources & evidence

ORD record
ord-ace10952b6344e5eb44dedf8bbbf28b2
Source dataset
uspto-grants-1980_03
Patent number
US04192950

Reaction notes

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