Reaktion #59888

Reaktionsgleichung

sodium hydroxide

2,3-dimethyl-4-(1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy)pyridine 1-oxide

acetic anhydride

→

title compound

Ausbeute 59.5%

(3-methyl-4-(1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy)pyridin-2-yl)methanol

Ausbeute 59.5%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooled to a room temperature
2. 2
   Einengenthe reaction mixture was concentrated
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for one hour
4. 4
   EinengenThe reaction mixture was concentrated
5. 5
   Sonstigethe residue was separated between water and ethyl acetate
6. 6
   WaschenThe organic layer was washed twice with a 1N aqueous sodium hydroxide solution
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated

Vorschrift

The 2,3-dimethyl-4-(1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy)pyridine 1-oxide (3.31 g, 10.7 mmol) obtained in the step (10b) was mixed with acetic anhydride (30 ml, 331 mmol). The mixture was stirred at 85° C. for 1 hour and 55 minutes. After cooled to a room temperature, the reaction mixture was concentrated. To the residue, methanol (50 ml) and a 5N aqueous sodium hydroxide solution (30 ml, 150 mmol) were added and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated and the residue was separated between water and ethyl acetate. The organic layer was washed twice with a 1N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain the title compound (1.97 g, yield: 59.5%) as a brown oil.

Quelle