Acetic Acid → 2-Acetoxymethyl-3-methyl-pyridine

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.

1. temperaturethe solution was heated at 70° C. overnight
2. temperatureto cool to room temperature
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in CHCl3 (100 mL)
5. additiontreated with solid Na2CO3 (14.12 g)
6. waitAfter 1 hour
7. customthe supernatant was decanted
8. washthe residue was washed with warm CHCl3 (3×50 mL)
9. filtrationThe combined supernatants were filtered
10. concentrationconcentrated
11. customto provide 4.6951 g as a yellow solid
12. temperatureheated at 90° C. overnight
13. temperatureThe mixture was cooled to room temperature
14. concentrationconcentrated
15. filtrationthe crude product was filtered through a silica plug (33 g silica, ethyl acetate)

ORDレコード

ord-b0ed2b81d0864736adc41f19e2b2dd94

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07084155B2