تفاعل #413371

معادلة التفاعل

(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

المذيبات

acetonitrile

ether

hexane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر