Imidazole → (But-3-enyloxy)(tert-butyl)dimethylsilane

HRID 1245337Notes

Reaction equation

HRID 1245337 reaction equation
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].N1C=CN=C1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([O:5][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:2][CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 693893-Buten-1-ol

Product 1

HCID 10008065(But-3-enyloxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of but-3-en-1-ol (2.39 mL, 27.73 mmol) in DMF was added imidazole (3.78 g, 55.46 mmol), and tert-butyldimethylsilyl chloride (6.3 g, 41.59 mmol). The mixture was stirred at room temperature overnight. Saturated NH4Cl was added and the mixture was extracted with ethyl acetate three times. Combined organic extracts were washed twice with water and brine then dried over Na2SO4. The solvent was evaporated in vacuo to give title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washCombined organic extracts were washed twice with water and brine
  3. dry with materialthen dried over Na2SO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-384ef07ac2a94318b3d0238aac3189a7
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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