Potassium Carbonate → 2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-3-methoxy-benzaldehyde

HRID 1728130Notes

Reaction equation

HRID 1728130 reaction equation
[I:1][C:2]1[C:3](O)=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13]([O-:16])([O-])=O.[K+].[K+].BrC[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O.C(OCC)(=O)C>[C:26]([Si:23]([CH3:25])([CH3:24])[O:22][CH2:21][CH2:13][O:16][C:5]1[C:4]([O:10][CH3:11])=[CH:3][C:2]([I:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 575659542-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-3-methoxy-benzaldehydeYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-iodovanillin (10 g, 35.9 mmol) (Aldrich) in N,N-dimethylformamide (150 mL) was added anhydrous K2CO3 (14.9 g, 108 mmol), and (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (10.3 g, 43 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, dried over MgSO4, concentrated, and purified by chromatography to give 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-3-methoxy-benzaldehyde as a yellow oil (Yield 15 g, 96%).

Workup

  1. temperatureThe crude was cooled to room temperature
  2. washwashed with water, brine
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-4348e8e7fe684d42b17a268558ed48fa
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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