Imidazole → HCID 22926880, compound

HRID 1985416Notes

Reaction equation

HRID 1985416 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:10][OH:11].N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>ClCCl.O>[Si:21]([O:11][CH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[F:1])[CH:6]=[O:7])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 229267584-Fluoro-3-(hydroxymethyl)benzaldehyde

Product 1

HCID 22926880HCID 22926880, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.6 g of 4-Fluoro-3-hydroxymethylbenzaldehyde was dissolved in 20 ml of dichloromethane, and 1.4 g of imidazole and 1.75 g of t-butyldimethylchlorosilane were added under ice-cooling, then the mixture was stirred at room temperature for 16 hours. The reaction solution was diluted with water and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography (18% ethyl acetate-hexane), to give 2.6 g of the title compound.

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-915e6b557f7c4f7e81d958575ff0af25
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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