Imidazole → Benzaldehyde, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 2243291Notes

Reaction equation

HRID 2243291 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:9](=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12].N1C=CN=C1.[OH-].[Na+]>CN(C=O)C.C1CCCCC1.CC(=O)OCC>[Si:1]([O:12][C:11]1[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=1[CH:9]=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6998SalicylaldehydeHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10900635Benzaldehyde, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

13.58 g (90.07 mmol) of t-butyidimethylsilyl chloride (TBDMSCl) were added to a solution of 10.00 g (81.89 mmol) of salicylaldehyde and 6.13 g (90.07 mmol) of imidazole in 82 ml of DMF. The mixture was stirred at room temperature and the reaction was monitored by thin-layer chromatography (cyclohexane/EA 10:1). 1 N NaOH was added, and the mixture was extracted with petroleum ether. The combined organic phases were dried over Na2SO4, the solvent was removed and the product was purified chromatographically (silica gel, cyclohexane/EA 10:1). This gave 16.94 g (87.5%) of a clear liquid.

Workup

  1. extractionthe mixture was extracted with petroleum ether
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customthe solvent was removed
  4. customthe product was purified chromatographically (silica gel, cyclohexane/EA 10:1)

Sources & evidence

ORD record
ord-9aef2b2a18e3448c8b58cc3269cfdd0f
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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