Pyridine → HCID 22797509, compound

Temperature

25 °C

Chromium trioxide (6.0 g., 0.06 mole) is added to a mechanically-stirred solution of dry pyridine (9.49 g., 0.12 mole) in methylene chloride (150 ml.) maintained at 0°-5° C. under a nitrogen atmosphere. The resulting reaction mixture is warmed to 25° C., stirred at 25° C. for 1/3 hour, and treated with a solution of 3(S)-benzyloxy-1-octanol (2.37 g., 0.01 mole) in methylene chloride (2 ml.) which initiates precipitation of a black, intractable precipitate. After stirring at 25° C. for 1/4 hour, the solution is decanted, and the insoluble precipitate washed with ether (200 ml.). The combined decantates are washed successively with 5% sodium hydroxide (3 × 100 ml.), 5% hydrochloric acid (100 ml.), and 5% aqueous sodium bicarbonate (100 ml.); dried over magnesium sulfate; and filtered. In vacuo evaporation of the filtrate affords the title compound as a pale yellow oil.

1. temperaturemaintained at 0°-5° C. under a nitrogen atmosphere
2. customThe resulting reaction mixture
3. customprecipitation of a black, intractable precipitate
4. stirringAfter stirring at 25° C. for 1/4 hour
5. customthe solution is decanted
6. washthe insoluble precipitate washed with ether (200 ml.)
7. washThe combined decantates are washed successively with 5% sodium hydroxide (3 × 100 ml.), 5% hydrochloric acid (100 ml.), and 5% aqueous sodium bicarbonate (100 ml.)
8. dry with materialdried over magnesium sulfate
9. filtrationand filtered
10. customIn vacuo evaporation of the filtrate

ORD record

ord-0ec4bcb1f91c4e7ea0dd1cfc6e641801

Source dataset

uspto-grants-1977_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04022794