Imidazole → HCID 57554606, compound

HRID 1511893Notes

Reaction equation

HRID 1511893 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:19])[CH2:16][CH:17]=[CH2:18])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=CN=C1.[C:25]([Si:29]([CH3:32])([CH3:31])Cl)([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([Si:29]([CH3:32])([CH3:31])[O:19][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=1)[CH2:16][CH:17]=[CH2:18])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57554608HCID 57554608, compound

Product 1

HCID 57554606HCID 57554606, compoundYield 115.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-octylphenyl)but-3-en-1-ol (11.5 g, 44.2 mmol) and imidazole (3.16 g, 46.4 mmol) were combined in DMF (221 ml). Tert-butyldimethylchlorosilane (6.66 g, 44.2 mmol) was added and the reaction stirred for about 72 h. The reaction was quenched by addition of water and ethyl acetate (500 mL). The layers were separated. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extracts were washed with 5% LiCl solution (3×). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to provide tert-butyldimethyl(1-(4-octylphenyl)but-3-enyloxy)silane (19.108 g, 51.0 mmol, 115% yield) as a colorless oil. LC/MS (method f) Rt=5.32, 3.89 min.; MS m/z: 243.21 (M-OTBDMS)+.

Workup

  1. customThe reaction was quenched by addition of water and ethyl acetate (500 mL)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  4. washThe combined ethyl acetate extracts were washed with 5% LiCl solution (3×)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f966c62dd3fa424fab7f8851346698c9
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

Loading…