Imidazole → 4-[(Tert-butyldimethylsilyl)oxy]-2-chlorobenzaldehyde

HRID 490850Notes

Reaction equation

HRID 490850 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C)C=O>[Si:11]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([Cl:1])[CH:9]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 589074694-[(Tert-butyldimethylsilyl)oxy]-2-chlorobenzaldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-4-hydroxybenzaldehyde (5.0 g, 32 mmol), tert-butyl(dimethyl)silyl chloride (5.3 g, 35 mmol), imidazole (2.9 g, 45 mmol) and N,N-dimethylaminopyridine (10 mg) in N,N-dimethylformamide (40 ml) was stirred at room temperature under a nitrogen atmosphere for 16 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acteate (100 ml) and water (100 ml). The organic phase was separated, washed with sat. aq. sodium chloride (50 ml), dried (sodium sulfate) and reduced in vacuo. Further purification by column chromatography on silica gel eluting with pentane:ethyl acetate (3:1 changing to 2:1) gave the title compound as a colourless oil (6.50 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acteate (100 ml) and water (100 ml)
  3. customThe organic phase was separated
  4. washwashed with sat. aq. sodium chloride (50 ml)
  5. dry with materialdried (sodium sulfate)
  6. customFurther purification by column chromatography on silica gel eluting with pentane:ethyl acetate (3:1 changing to 2:1)

Sources & evidence

ORD record
ord-f8bd435fc73545899cf6b58acab18264
Source dataset
uspto-grants-2009_05
Patent number
US07528170B2

Reaction notes

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