Methanol → Penclomedine

A 50.0 g portion (0.15 mol) of 2,3,4,5-tetrachloro-6-(trichloromethyl)pyridine was dissolved in 50 ml of warm dimethyl sulfoxide and 100 ml of methanol was added. Sodium methoxide (68.5 ml of 25 percent solution in methanol, 0.30 mol) was added, with stirring, over a 30 minute period and the resulting mixture was heated to reflux, with stirring, for two hours. After cooling, the mixture was poured into ice water and the aqueous mixture was extracted twice with methylene chloride. The extract was washed with water and evaporated to remove the methylene chloride. Traces of dimethyl sulfoxide remained. The residue was dissolved in ether and the ethereal solution was washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to obtain 39.4 g of white solid product (81 percent of theory) melting at 67°-69° C. The proton nmr spectrum was consistent with the structure given.

1. temperaturethe resulting mixture was heated
2. temperatureto reflux
3. stirringwith stirring, for two hours
4. temperatureAfter cooling
5. extractionthe aqueous mixture was extracted twice with methylene chloride
6. washThe extract was washed with water
7. customevaporated
8. customto remove the methylene chloride
9. dissolutionThe residue was dissolved in ether
10. washthe ethereal solution was washed with water
11. dry with materialdried over magnesium sulfate
12. customevaporated under reduced pressure

ORD-Eintrag

ord-fd1322b11ed8470093839001a6f2fbef

Quelldatensatz

uspto-grants-1988_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04717726