Imidazole → HCID 23001298, compound

HRID 397994Notes

Reaction equation

HRID 397994 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([Si:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:15]([C:11]([CH3:14])([CH3:13])[CH3:12])([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 23001298HCID 23001298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-5-hydroxybenzaldehyde (4.66 g, 23.2 mmol), tert-butyldiphenylchlorosilane (7.73 mL, 30.6 mmol), and imidazole (2.37 g, 34.8 mmol) in DMF (50 mL) was stirred at 25° C. for 12 hours and 60° C. for 12 hours. The solvent was removed in vacuo and the residue partitioned between methylene chloride (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The layers were separated and the aqueous layer was extracted with methylene chloride (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (10% ethyl acetate/hexane) to provide the title compound as a yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between methylene chloride (100 mL) and saturated aqueous sodium bicarbonate (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride (3×100 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7ef136b616f04e169dbc007f05816763
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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