Acetic Anhydride → HCID 13654799, compound

Temperature

110 °C

To a solution of 2,3-dimethyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine-1-oxide (2.6 g) in acetic anhydride (8 ml), concentrated sulfuric acid (2 drops) was added; and the solution was stirred at 110° C. for 4 hours and then concentrated. The resulting residue was dissolved in methanol (20 ml) and a solution of sodium hydroxide (1.2 g) in water (5 ml) was added, after which the mixture was stirred at room temperature for 30 minutes. After concentration, water was added, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and the solvent was evaporated, after which the resulting residue was applied on a silica gel (50 g) column, eluted with chloroform-methanol (10:1) and then recrystallized from isopropyl ether to give 1.6 g of 2-hydroxymethyl-3-methyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine as yellow crystals (melting points: 67°~68° C.).

1. concentrationconcentrated
2. dissolutionThe resulting residue was dissolved in methanol (20 ml)
3. additiona solution of sodium hydroxide (1.2 g) in water (5 ml) was added
4. stirringafter which the mixture was stirred at room temperature for 30 minutes
5. concentrationAfter concentration, water
6. additionwas added
7. extractionthe mixture was extracted with ethyl acetate
8. dry with materialThe extract was dried over magnesium sulfate
9. customthe solvent was evaporated
10. washeluted with chloroform-methanol (10:1)
11. customrecrystallized from isopropyl ether

ORD record

ord-d612739120984feeb1b6517f448ca476

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04769456