Imidazole → {3-[3-(Benzyloxy)phenyl]propoxy}(tert-butyl)dimethylsilane

HRID 2389367Notes

Reaction equation

HRID 2389367 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][OH:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][O:18][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 126481553-(Phenylmethoxy)benzenepropanol

Product 1

HCID 68535354{3-[3-(Benzyloxy)phenyl]propoxy}(tert-butyl)dimethylsilaneYield 116.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[3-(benzyloxy)phenyl]-1-propanol (1.73 g) in DMF (20 mL) were added imidazole (1.07 g) and tert-butyldimethylchlorosilane (1.83 g) at ambient temperature and the mixture was stirred at the same temperature for 2 hours. Water (20 mL) was added to the mixture at ambient temperature and the mixture was extracted with EtOAc (20 mL) two times. The organic layer was washed successively with 12% NaCl aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford {3-[3-(benzyloxy)phenyl]propoxy}(tert-butyl)dimethylsilane (2.96 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (20 mL) two times
  2. washThe organic layer was washed successively with 12% NaCl aqueous solution and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-453620c1fa57487b9625657e105c8ec5
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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