Reacción #413371

Ecuación de reacción

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

triphenylphosphine

carbon tetrachloride

pyridine

→

desired compound

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

Disolventes

acetonitrile

ether

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered
2. 2
   OtroThe residue from the evaporation
3. 3
   Extracciónwas extracted with a mixture of 5 ml of ether and 95 ml of hexane
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated to dryness under vacuum
6. 6
   OtroThe residue was purified by column chromatography on silica gel with hexane/20-50% ethyl acetate as the eluent

Procedimiento

A solution of 1.15 g of (5Z,13E)-(8R,9S,11R,12R,15R)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)-16,16,19-trimethyl-5,13,18-prostatrienoic acid methyl ester, 780 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 for 55 hours under argon at room temperature. The mixture was then diluted with 15 ml of ether and 30 ml of hexane, further stirred for 10 minutes, and filtered. The residue from the evaporation 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/20-50% ethyl acetate as the eluent, thus obtaining 1.07 g of the desired compound.

Fuente