Imidazole → Silane, (1,1-dimethylethyl)[(1,1-dimethyl-2-propynyl)oxy]dimethyl-

HRID 275516Notes

Reaction equation

HRID 275516 reaction equation
[OH:1][C:2]([CH3:6])([CH3:5])[C:3]#[CH:4].N1C=CN=C1.[C:12]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])([CH3:14])[CH3:13].CN(C1C=CC=CN=1)C>O.CN(C)C=O>[C:12]([Si:16]([CH3:18])([CH3:17])[O:1][C:2]([CH3:6])([CH3:5])[C:3]#[CH:4])([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 82582-Methyl-3-butyn-2-olHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11084826Silane, (1,1-dimethylethyl)[(1,1-dimethyl-2-propynyl)oxy]dimethyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To the stirred mixture of 25 g (0.29M) of 3-hydroxy-3-methyl-butyne, 50 ml of anhydrous N,N-dimethyl-formamide and 44.5 g (0.65M) imidazole cooled in an ice-bath was added 50 g (0.33M) tert.butyldimethylsilyl chloride. Stirring in the ice-bath was continued for 15 minutes and then at room temperate overnight. After addition of 250 mg of dimethylaminopyridine, the reaction mixture was heated at 70° C. for two hours and then poured into one liter of cold water. It was then extracted with 5×150 ml of ether. The organic extract was washed with brine, dried over MgSO4 and evaporated to dryness. The crude product was purified by vacuum distillation yielding 3-(tert.butyldimethylsilyl)oxy-3-methyl-butyne.

Workup

  1. temperaturecooled in an ice-bath
  2. customat room temperate overnight
  3. extractionIt was then extracted with 5×150 ml of ether
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. distillationThe crude product was purified by vacuum distillation

Sources & evidence

ORD record
ord-f69c70ff0ecf4675a7da9550d3540cac
Source dataset
uspto-grants-1995_02
Patent number
US05393900

Reaction notes

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