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Chromic Acid → (13E)-(11alpha,15S)-6,9-Dioxo-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

HRID 1277700
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1277700
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:38])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:12][C@@H:11]1[OH:37].[Cr](O)(O)(=O)=O>C(OCC)C>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:38])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:12][C:11]1=[O:37]
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Komponenten

4

Edukt 2

HCID 24425Chromic AcidHCID 70575053(13E)-(9alpha,11alpha,15S)-6-Oxo-9-hydroxy-11,15-bis-(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

Produkt 1

HCID 70575454(13E)-(11alpha,15S)-6,9-Dioxo-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of crude (13E)-(9α,11α,15S)-6-oxo-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Reference Example 7) in 10 ml of diethyl ether was added 10 ml of a chromic acid solution (obtained from 760 mg of chromium trioxide, 2.56 g of manganese sulphate, 0.84 ml of sulphuric acid and 19 ml of water) at 0° to 5° C., and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was extracted with diethyl ether and the extract was washed with an aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of n-hexane and ethyl acetate (17:3) as eluent to give 480 mg of the title compound having the following physical characteristic:

Aufarbeitung

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. washthe extract was washed with an aqueous solution of sodium bicarbonate
  3. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of n-hexane and ethyl acetate (17:3) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-bc194f7592e44a609bc0c44aa888dfe5
Quelldatensatz
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04278688

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