反応 #413365

反応方程式

(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

収率 42.0%

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

収率 42.0%

溶媒

methylene chloride

ethanol

反応条件

後処理

1. 1
   洗浄washed twice with saturated sodium chloride solution
2. 2
   乾燥dried over magnesium sulfate
3. 3
   その他evaporated to dryness under vacuum
4. 4
   その他The residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the eluent

実験手順

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.

出典