Imidazole → HCID 57857736, compound

HRID 607490Notes

Reaction equation

HRID 607490 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][C:17]([CH:21]=[O:22])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CN=C1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O.ClCCl>[Si:23]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][C:17]([CH:21]=[O:22])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 24436Sodium SulfateHCID 28928tert-Butyldimethylsilyl chlorideHCID 57857727HCID 57857727, compound

Product 1

HCID 57857736HCID 57857736, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

9-(6-hydroxyhexyl)-9H-carbazole-3-carbaldehyde (12.0 g, 0.0406 mol) and dichloromethane (100 ml) were loaded into a three-neck flask, stirred, added with tert-butyldimethylsilyl chloride (7.35 g, 0.0487 mol) and imidazole (3.04 g, 0.0447 mol), and allowed to react at room temperature for 24 hours with stirring. The reaction product was transferred into a separate funnel, and was then added with water and ethyl acetate, after which the organic layer was isolated therefrom, dehydrated using sodium sulfate, and then distilled under reduced pressure. Then, the obtained viscous liquid was separated through silica column chromatography, thus obtaining 10.8 g of a liquid as the title compound.

Workup

  1. customto react at room temperature for 24 hours
  2. stirringwith stirring
  3. customThe reaction product was transferred into a separate funnel
  4. customafter which the organic layer was isolated
  5. distillationdistilled under reduced pressure
  6. customThen, the obtained viscous liquid was separated through silica column chromatography

Sources & evidence

ORD record
ord-8a9c664d749b46608f05ee921330dc57
Source dataset
uspto-grants-2011_03
Patent number
US07915428B2

Reaction notes

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