1,2-Dimethoxyethane → 4-(Trimethylsilyl)benzaldehyde

HRID 1768558Notes

Reaction equation

HRID 1768558 reaction equation
Br[CH:2](Br)[C:3]1[CH:8]=[CH:7][C:6]([Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.C(COC)[O:15]C>O.[N+]([O-])([O-])=O.[Ag+]>[CH3:10][Si:9]([CH3:12])([CH3:11])[C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[O:15])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 23207303HCID 23207303, compound

Product 1

HCID 6375734-(Trimethylsilyl)benzaldehydeYield 99%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

The product of Step A (10 g, 30 mmole) was dissolved in dimethoxyethane (160 mL) and heated to reflux. A solution of silver nitrate (15.3 g, 90 mmole) in water (120 mL) was added dropwise while maintaining reflux. The reaction mixture was heated for 30 additional minutes and then cooled and the liquid decanted away from the percipitate. The solid was triturated with ether and the combined organic phases were washed once with water, dried (MgSO4), and concentrated to give the desired product as a pale yellow oil (6 g, 99% yield).

Workup

  1. temperatureheated to reflux
  2. temperaturewhile maintaining
  3. temperaturereflux
  4. temperatureThe reaction mixture was heated for 30 additional minutes
  5. temperaturecooled
  6. customthe liquid decanted away from the percipitate
  7. customThe solid was triturated with ether
  8. washthe combined organic phases were washed once with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1fa5083d3cec4c2597ff2539994a824d
Source dataset
uspto-grants-1995_01
Patent number
US05378708

Reaction notes

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