4-Hydroxybenzaldehyde → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 736859Notes

Reaction equation

HRID 736859 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CO>C(#N)C>[Si:15]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 887MethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-hydroxybenzaldehyde (8.21 g, 67.2 mmol) was dissolved in acetonitrile (164 ml) in nitrogen atmosphere, and imidazole (6.87 g, 100.8 mmol) was added at room temperature. Tert-butyldimethylsilyl chloride was added under cooling with ice, followed by stirring for 30 minutes. Methanol was added to terminate the reaction, the reaction solution was subjected to filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 4-(tert-butyldimethylsilyloxy)benzaldehyde (15.23 g, 96%) as a pale yellow oily substance.

Workup

  1. additionwas added at room temperature
  2. temperatureunder cooling with ice
  3. customto terminate
  4. customthe reaction
  5. filtrationthe reaction solution was subjected to filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-7e793fb192ed4aaf82eb5c51786fdf4f
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

Loading…