Reacción #413365

Ecuación de reacción

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

pyridine p-toluenesulfonate

→

carboxylic acid

Rendimiento 42.0%

(5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-5,13,18-prostatrienoic Acid

Rendimiento 42.0%

Disolventes

methylene chloride

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed twice with saturated sodium chloride solution
2. 2
   Secadodried over magnesium sulfate
3. 3
   Otroevaporated to dryness under vacuum
4. 4
   OtroThe residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the eluent

Procedimiento

A solution of 144 mg of (5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid in 2 ml of absolute ethanol was combined with 6.4 mg of pyridine p-toluenesulfonate and agitated for 5 days at room temperature under argon. The reaction mixture was then diluted with 100 ml of methylene chloride, washed twice with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the eluent, thus obtaining 42.5 mg of the desired carboxylic acid as a highly viscous oil.

Fuente