Imidazole → HCID 17842500, compound

HRID 459531Notes

Reaction equation

HRID 459531 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.N1C=CN=C1.[C:14]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15].CO>CN(C)C=O>[Si:18]([O:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 155123-Cyclohexene-1-methanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 17842500HCID 17842500, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Cyclohexene-1-methanol (5.0 g) was dissolved in N,N-dimethylformamide (50 ml), and imidazole (3.93 g) and tert-butylchlorodiphenylsilane (14 ml) were added to stir the mixture for 22 hours. After adding methanol, the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=30:1) to obtain (±)-4-(tert-butyldiphenylsilyloxymethyl)-1-cyclohexene (16.1 g) as a colorless oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionextraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-7b939e8cf1514c2aa8e6b48ea2a5091c
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

Loading…