Acetic Anhydride → HCID 59792534, compound

Temperature

85 °C

The 4-(5,9-dioxaspiro[3.5]non-7-ylmethoxy)-2,3,5-trimethylpyridine 1-oxide (1.97 g, 6.72 mmol) obtained in the step (13b) was mixed with acetic anhydride (20 ml, 212 mmol). The mixture was stirred at 85° C. for 1.5 hours. After cooled to room temperature, the reaction mixture was concentrated. To the residue, methanol (20 ml) and a 5N aqueous sodium hydroxide solution (20 ml, 100 mmol) were added and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The organic layer was washed with a 2N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain the title compound (1.69 g, yield: 85.7%) as a brown oil.

1. temperatureAfter cooled to room temperature
2. concentrationthe reaction mixture was concentrated
3. stirringthe mixture was stirred at room temperature for 45 minutes
4. concentrationThe reaction mixture was concentrated
5. customthe residue was partitioned between water and ethyl acetate
6. washThe organic layer was washed with a 2N aqueous sodium hydroxide solution
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-28363176e5e14583858fde116548cad3

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124780B2