Imidazole → HCID 86724349, compound

HRID 2274278Notes

Reaction equation

HRID 2274278 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CN=C1.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21].CCCCCC.C(OCC)(=O)C>CN(C=O)C.O>[C:20]([Si:23]([CH3:25])([CH3:24])[O:11][CH2:10][CH2:9][O:8][C:7]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([CH3:22])([CH3:21])[CH3:19]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 853812-(4-Nitrophenoxy)ethanolHCID 21226206Ethyl acetate hexane

Product 1

HCID 86724349HCID 86724349, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-nitrophenoxy)ethanol (6.40 g) in DMF were added imidazole (4.75 g) and TBDMSCl (6.84 g) and reaction mixture was stirred at room temperature for 1 hr. The reaction was monitored on TLC using hexane:ethyl acetate (7:3) as mobile phase. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent removed under reduced pressure. The crude material was purified by column chromatography eluted with 6% ethyl acetate in hexane to give, after concentration, 10 g of tert-butyldimethyl(2-(4-nitrophenoxy)ethoxy)silane.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe crude material was purified by column chromatography
  6. washeluted with 6% ethyl acetate in hexane
  7. customto give
  8. concentrationafter concentration, 10 g of tert-butyldimethyl(2-(4-nitrophenoxy)ethoxy)silane

Sources & evidence

ORD record
ord-35928c21254f4ca289fc7470bf44cba4
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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