Reacción #413375

Ecuación de reacción

(5Z,13E,18Z)-(8R,9S,11R,12R,15S,16RS)-9-hydroxy-19-chloro-16-methyl-11,15-bis(tetrahydropyran-2-yloxy)-5,13,18-prostatrienoic acid methyl ester

triphenylphosphine

carbon tetrachloride

pyridine

→

desired compound

(5Z,13E,18Z)-(8R,9R,11R,12R,15S,16RS)-9,19-Dichloro-16-methyl-11,15-bis(tetrahydropyran-2-yloxy)-5,13,18-prostatrienoic Acid Methyl Ester

Disolventes

acetonitrile

ether

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered
2. 2
   ExtracciónThe evaporation residue was extracted with a mixture of 5 ml of ether and 95 ml of hexane
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated to dryness under vacuum
5. 5
   OtroThe residue was purified by column chromatography on silica gel with hexane/10-50% ethyl acetate as the eluent

Procedimiento

A solution of 1.16 g of (5Z,13E,18Z)-(8R,9S,11R,12R,15S,16RS)-9-hydroxy-19-chloro-16-methyl-11,15-bis(tetrahydropyran-2-yloxy)-5,13,18-prostatrienoic acid methyl ester, 785 mg of triphenylphosphine, and 15 ml of a solution of 0.97 ml of carbon tetrachloride, 0.79 ml of pyridine, and 48 ml of acetonitrile was stirred under argon at room temperature for 65 hours. The mixture was then diluted with 15 ml of ether and 30 ml of hexane, further stirred for 10 minutes, and filtered. The evaporation residue was extracted with a mixture of 5 ml of ether and 95 ml of hexane, filtered, and concentrated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/10-50% ethyl acetate as the eluent. In this way, 457 mg of the desired compound was isolated.

Fuente