Potassium Carbonate → 2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde

HRID 1728070Notes

Reaction equation

HRID 1728070 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C)C=O.C(OCC)(=O)C>[C:24]([Si:21]([CH3:23])([CH3:22])[O:20][CH2:19][CH2:18][O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 575659162-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehydeYield 99.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-chlorosalicylaldehyde (5 g, 32 mmol) (Aldrich) in N,N-dimethylformamide (40 mL) was added potassium carbonate (20 g, 145 mmol), and (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (10 g, 42 mmol, Aldrich). The reaction mixture was heated at 60° C. for 18 h. The crude was cooled to room temperature, diluted with ethyl acetate, washed with water, brine. The organic layer was separated, concentrated, and the residue was purified by chromatography (EtOAc:Hexanes=1:8, then 1:4) to give 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde as a white solid (Yield 10 g, 99%).

Workup

  1. temperatureThe crude was cooled to room temperature
  2. washwashed with water, brine
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customthe residue was purified by chromatography (EtOAc

Sources & evidence

ORD record
ord-8e8e8511a3b5490fb33e42a8918302da
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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