Réaction #172390

Équation de réaction

compound

3-(2-Hydroxyethyl)-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

imidazole

tert-butyl(chloro)diphenylsilane

→

3-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

Solvants

N,N-dimethylformamide

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted three times with ethyl acetate
2. 2
   LavageThe combined organic phases are washed twice with water
3. 3
   Séchagedried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreFor crystallization, tert-butyl methyl ether
7. 7
   workup.ADDITIONis added
8. 8
   Filtrationthe resulting crystals are filtered off
9. 9
   Autredried under reduced pressure

Mode opératoire

24 g (81 mmol) of the compound from Example 21A are dissolved in 200 ml of anhydrous N,N-dimethylformamide, and 7.2 g (106 mmol) of imidazole and 27 g (98 mmol) of tert-butyl(chloro)diphenylsilane are added. After 16 h, the mixture is diluted with 1.2 l of water and extracted three times with ethyl acetate. The combined organic phases are washed twice with water, dried over magnesium sulphate, filtered and concentrated under reduced pressure. For crystallization, tert-butyl methyl ether is added, and the resulting crystals are filtered off and dried under reduced pressure. This gives 30 g (67% of theory) of the desired product.

Source