tert-Butyldimethylsilyl chloride → 3-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethoxy)benzaldehyde

HRID 1295730Notes

Reaction equation

HRID 1295730 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]>CN(C=O)C.O>[C:2]([Si:5]([CH3:7])([CH3:6])[O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17])([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 6453965Benzaldehyde, 3-(2-hydroxyethoxy)-

Product 1

HCID 714171133-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethoxy)benzaldehydeYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

TBDMSCl silylation reagent in DMF (60 mL) was added to 3-(2-hydroxy-ethoxy)-benzaldehyde (4.985 g, 30.00 mmol). The mixture was stirred at room temperature for 72 h. The mixture was diluted with water and extracted with diethyl ether. The ethereal extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by SiO2 eluted with 95:5 CH2Cl2/MeOH to give 2.38 g (28%) of a clear oil.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe ethereal extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by SiO2
  5. washeluted with 95:5 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-5d86f8bdad9f4631a89b599cbaab0a5f
Source dataset
uspto-grants-2007_07
Patent number
US07244738B2

Reaction notes

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