Imidazole → HCID 17842500, compound

HRID 546475Notes

Reaction equation

HRID 546475 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-butyldiphenylsilyloxy-methyl)-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-3fa1203d12a940389a2db68ef6f74eb9
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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