反応 #7239

反応方程式

H2O2

2,3-lutidine

H2O2

acetic acid

→

2-acetoxymethyl-3-methyl-pyridine

溶媒

acetic anhydride

反応条件

後処理

1. 1
   温度the solution was heated at 70° C. overnight
2. 2
   温度to cool to room temperature
3. 3
   濃縮concentrated 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
   その他the supernatant was decanted
8. 8
   洗浄the residue was washed with warm CHCl3 (3×50 mL)
9. 9
   ろ過The combined supernatants were filtered
10. 10
    濃縮concentrated
11. 11
    その他to provide 4.6951 g as a yellow solid
12. 12
    温度heated at 90° C. overnight
13. 13
    温度The mixture was cooled to room temperature
14. 14
    濃縮concentrated
15. 15
    ろ過the crude product was filtered through a silica plug (33 g silica, ethyl acetate)

実験手順

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.

出典