Imidazole → Silane, [(1-ethynylcyclohexyl)oxy]trimethyl-

HRID 426618Notes

Reaction equation

HRID 426618 reaction equation
N1C=CN=C1.[C:6]([C:8]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7].CN(C)C=O.[CH3:20][Si:21]([CH3:24])([CH3:23])Cl>CCCCCC>[C:6]([C:8]1([O:14][Si:21]([CH3:24])([CH3:23])[CH3:20])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 65251-Ethynylcyclohexanol

Product 1

HCID 552482Silane, [(1-ethynylcyclohexyl)oxy]trimethyl-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 194 g portion of imidazole and 158.2 g of 1-ethynylcyclohexan-1-ol are mixed with 500 g of dimethylformamide with cooling in an ice bath. A 152 g portion of trimethylchlorosilane is added with cooling and stirring in about one minute. The mixture is stirred for one hour and allowed to stand overnight. One liter of hexane is added. The lower layer is separated, diluted with water and extracted with hexane. The hexane layers are washed several times with water and then combined and dried over magnesium sulfate. Filtration and then evaporation of the hexane gives 198.5 g of product which is distilled giving 168 g of the desired product.

Workup

  1. temperaturewith cooling in an ice bath
  2. temperaturewith cooling
  3. stirringThe mixture is stirred for one hour
  4. waitto stand overnight
  5. customThe lower layer is separated
  6. additiondiluted with water
  7. extractionextracted with hexane
  8. washThe hexane layers are washed several times with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationFiltration
  11. customevaporation of the hexane

Sources & evidence

ORD record
ord-97dc682c550549ecb41e24e18628d955
Source dataset
uspto-grants-1979_10
Patent number
US04170597

Reaction notes

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