Imidazole → t-Butylpent-4-ynyloxy diphenyl silane

HRID 128760Notes

Reaction equation

HRID 128760 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:24]([OH:29])[CH2:25][CH2:26][C:27]#[CH:28]>CN(C=O)C.O>[Si:6]([O:29][CH2:24][CH2:25][CH2:26][C:27]#[CH:28])([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 793464-Pentyn-1-olHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 5461495t-Butylpent-4-ynyloxy diphenyl silaneYield 1,265.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Imidazole (9.29 g (136 mmol) was dissolved in 50 ml of DMF under nitrogen with stirring. To this solution was added 18.75 g (17.74 mmol) of t-butyldiphenylsilyl chloride and 5.27 g (5.55 mmol) of 4-pentyn-1-ol and the mixture was stirred at room temperature for 2 h. The mixture was carefully diluted with 300 ml of water, extracted with ethyl acetate, and the organic layer was washed with water, brine, and dried over magnesium sulfate. The organic solution was concentrated in vacuo to provide 22.66 g of a yellow oil which was purified by passing through 150 g pad of silica gel eluting with hexane and 3% ethyl acetate in hexane affording 17.56 g (86.8%) of the title compound as a clear oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-d24ddd449af841e7b52901a9974c68c3
Source dataset
uspto-grants-1995_11
Patent number
US05464848

Reaction notes

Loading…