반응 #413365

ord-c98d9cf42f884f8caf14e63d9f3ac74f

반응 방정식

$CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1$

(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

→

$CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](Cl)C[C@H]1O$

carboxylic acid

수율 42.0%

$CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](Cl)C[C@H]1O$

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

수율 42.0%

반응물

$CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1$

(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

시약

없음

용매

methylene chloride

ethanol

반응 조건

상세 조건

See reaction.notes.procedure_details.

후처리

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

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04444788uspto-grants-1984_04