Réaction #465940

Équation de réaction

2,3-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)-pyridine-1-oxide

acetic anhydride

→

2-hydroxymethyl-3-methyl-4-(2,2,3,3, 3-pentafluoropropoxy)pyridine

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (30 ml)
3. 3
   workup.ADDITION2 N aqueous sodium hydroxide (20 ml) was added
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hours
5. 5
   ConcentrationAfter concentration, water
6. 6
   workup.ADDITIONwas added to the residue
7. 7
   Extractionthe mixture was extracted with ethyl acetate
8. 8
   SéchageThe extract was dried over magnesium sulfate
9. 9
   workup.DISTILLATIONthe solvent was then distilled off
10. 10
    LavageElution
11. 11
    Autrewith chloroform-methanol (10:1) and recrystallization from isopropyl ether

Mode opératoire

Concentrated sulfuric acid (2 drops) was added to a solution 2,3-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)-pyridine-1-oxide (2.5 g) in acetic anhydride (8 ml) and the mixture was stirred at 110° C. for 2 hours and then concentrated. The residue was dissolved in methanol (30 ml), 2 N aqueous sodium hydroxide (20 ml) was added, and the mixture was stirred at room temperature for 2 hours. After concentration, water was added to the residue and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, the solvent was then distilled off, and te residue was applied to a silica gel (50 g) column. Elution with chloroform-methanol (10:1) and recrystallization from isopropyl ether gave 1.6 g of 2-hydroxymethyl-3-methyl-4-(2,2,3,3, 3-pentafluoropropoxy)pyridine as a brown oil.

Source