Reaktion #7239

Reaktionsgleichung

H2O2

2,3-lutidine

H2O2

acetic acid

→

2-acetoxymethyl-3-methyl-pyridine

Lösungsmittel

acetic anhydride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was heated at 70° C. overnight
2. 2
   Temperaturto cool to room temperature
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in CHCl3 (100 mL)
5. 5
   workup.ADDITIONtreated with solid Na2CO3 (14.12 g)
6. 6
   workup.WAITAfter 1 hour
7. 7
   Sonstigethe supernatant was decanted
8. 8
   Waschenthe residue was washed with warm CHCl3 (3×50 mL)
9. 9
   FiltrationThe combined supernatants were filtered
10. 10
    Einengenconcentrated
11. 11
    Sonstigeto provide 4.6951 g as a yellow solid
12. 12
    Temperaturheated at 90° C. overnight
13. 13
    TemperaturThe mixture was cooled to room temperature
14. 14
    Einengenconcentrated
15. 15
    Filtrationthe crude product was filtered through a silica plug (33 g silica, ethyl acetate)

Vorschrift

To a stirred solution of 2,3-lutidine (4.8363 g, 45.13 mmol) in glacial acetic acid (30 mL) at room temperature was added 30% H2O2 (4.6 mL) and the resultant solution was heated to 70° C. After 6 hours, the reaction mixture was cooled to room temperature, additional H2O2 (4.6 mL) was added, and the solution was heated at 70° C. overnight. The reaction mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was dissolved in CHCl3 (100 mL) and treated with solid Na2CO3 (14.12 g). After 1 hour, the supernatant was decanted and the residue was washed with warm CHCl3 (3×50 mL). The combined supernatants were filtered and concentrated to provide 4.6951 g as a yellow solid. The solid was dissolved in acetic anhydride (38 mL) and heated at 90° C. overnight. The mixture was cooled to room temperature and concentrated and the crude product was filtered through a silica plug (33 g silica, ethyl acetate) to give 6.13 g of 2-acetoxymethyl-3-methyl-pyridine as an orange oil.

Quelle