تفاعل #7239

معادلة التفاعل

H2O2

2,3-lutidine

H2O2

acetic acid

→

2-acetoxymethyl-3-methyl-pyridine

المذيبات

acetic anhydride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution was heated at 70° C. overnight
2. 2
   درجة الحرارةto cool to room temperature
3. 3
   تركيزconcentrated 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
   أخرىthe supernatant was decanted
8. 8
   غسيلthe residue was washed with warm CHCl3 (3×50 mL)
9. 9
   ترشيحThe combined supernatants were filtered
10. 10
    تركيزconcentrated
11. 11
    أخرىto provide 4.6951 g as a yellow solid
12. 12
    درجة الحرارةheated at 90° C. overnight
13. 13
    درجة الحرارةThe mixture was cooled to room temperature
14. 14
    تركيزconcentrated
15. 15
    ترشيحthe crude product was filtered through a silica plug (33 g silica, ethyl acetate)

الإجراء التجريبي

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.

المصدر