Reaction #40571

Reaction equation

5-bromo-2-hydroxy-3-methoxybenzaldehyde

potassium carbonate

(2-chloromethoxyethyl)trimethylsilane

→

5-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde

Solvents

DMF

Conditions

Workup

1. 1
   workup.DISTILLATIONThe DMF is distilled off in vacuo
2. 2
   workup.DISSOLUTIONthe residue is dissolved in ethyl acetate
3. 3
   Extractionthe resulting solution is extracted with water
4. 4
   DryingIt is then dried over magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   workup.DISTILLATIONthe solvent is distilled off
7. 7
   OtherThe crude product is purified by silica gel chromatography (heptane/ethyl acetate)

Procedure

10 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde, 23.9 g of potassium carbonate and 12.2 g of (2-chloromethoxyethyl)trimethylsilane is suspended in 500 ml of DMF and stirred at room temperature for 48 hours. The DMF is distilled off in vacuo, the residue is dissolved in ethyl acetate, and the resulting solution is extracted with water. It is then dried over magnesium sulphate and filtered, and the solvent is distilled off. The crude product is purified by silica gel chromatography (heptane/ethyl acetate).

Source