Imidazole → {[4-(1-Fluoroethenyl)oct-1-yn-4-yl]oxy}(trimethyl)silane

HRID 1154930Notes

Reaction equation

HRID 1154930 reaction equation
[F:1][C:2]([C:4]([OH:12])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][C:6]#[CH:7])=[CH2:3].N1C=CN=C1.CN(C)C=O.Cl[Si:24]([CH3:27])([CH3:26])[CH3:25]>O>[F:1][C:2]([C:4]([O:12][Si:24]([CH3:27])([CH3:26])[CH3:25])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][C:6]#[CH:7])=[CH2:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 127861924-(1-Fluoroethenyl)oct-1-yn-4-ol

Product 1

HCID 12801788{[4-(1-Fluoroethenyl)oct-1-yn-4-yl]oxy}(trimethyl)silane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred 0° C. solution of 13.7 g. of 4-(1-fluorovinyl)-4-hydroxy-1-octyne and 16.1 g. of imidazole in 60 ml. of anhydrous dimethylformamide is added, via a syringe over a 3 minute period, 11.6 ml. of chlorotrimethylsilane. The resulting solution is stirred at room temperature for 18 hours, cooled to 0° C., diluted with 350 ml of petroleum ether and shaken with 150 ml. of water. The organic phase is separated, washed with six 50 ml. portions of water, then 50 ml. of brine, dried over magnesium sulfate and concentrated in vacuo giving 18.9 g. of the desired product as a colorless liquid.

Workup

  1. customTo a stirred 0° C.
  2. temperaturecooled to 0° C.
  3. stirringshaken with 150 ml
  4. customThe organic phase is separated
  5. washwashed with six 50 ml
  6. dry with materialof brine, dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customgiving 18.9 g

Sources & evidence

ORD record
ord-8e69bff07d1947baa9107ae416ad0ca5
Source dataset
uspto-grants-1981_11
Patent number
US04298754

Reaction notes

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