Imidazole → 4-(2-(Tert-butyldimethylsilyloxy)ethoxy)benzaldehyde

HRID 23710

Reaction equation

HRID 23710 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].CCCCCC>CN(C=O)C.C(OCC)(=O)C>[Si:18]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8058HexaneHCID 28928tert-Butyldimethylsilyl chloride2×HCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-

Product 1

HCID 579561014-(2-(Tert-butyldimethylsilyloxy)ethoxy)benzaldehydeYield 49.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-(2-hydroxyethoxy)benzaldehyde (commercial, 0.5 g, 3 mmol) dissolved in DMF (10 mL) is added imidazole (0.4 g, 6 mmol) and tert-butyldimethylsilylchloride (0.53 g, 3.5 mmol). Reaction mixture is stirred for 20 h. at room temperature. TLC analysis (hexane:ethyl acetate,7:3) shows small amounts of unreacted starting material. Additional tert-butyldimethylsilylchloride (0.25 g, 1 mmol) is added and stirring continued for 16 h. The reaction is quenched with saturated aqueous ammonium chloride (20 mL) and diluted further with ethyl ether (20 mL). Aqueous layer is separated and extracted thrice with ether (10 mL). Combined organics dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel using a gradient of 2% to 5% ethyl acetate in hexanes to provide 0.42 g of the title compound.

Workup

  1. customReaction mixture
  2. stirringstirring
  3. waitcontinued for 16 h
  4. customThe reaction is quenched with saturated aqueous ammonium chloride (20 mL)
  5. additiondiluted further with ethyl ether (20 mL)
  6. customAqueous layer is separated
  7. extractionextracted thrice with ether (10 mL)
  8. dry with materialCombined organics dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified by flash chromatography on silica gel using a gradient of 2% to 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-80c3f0ea60a240ea855be153730b5b6d
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

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