Tetrahydropyranyl ether → Tetrahydropyranyl ether

HRID 1395808

Reaktionsgleichung

Reaktionsgleichung von HRID 1395808
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:26])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])[C@@H:12]([OH:24])[CH2:11][C@H:10]1[OH:25].[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:26])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])[C:12](=[O:24])[CH2:11][C@H:10]1[OH:25].[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1

Komponenten

6

Edukt 3

HCID 263182Tetrahydropyranyl etherHCID 52808886-Ketoprostaglandin F1 alphaHCID 131709961Jones' reagent

Produkt 2

HCID 263182Tetrahydropyranyl etherHCID 52808896-Keto-PGE1

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The reaction product from part A, containing 6-keto-PGF1α, bis(tetrahyropyranyl)ether, methyl ester corresponding to formula IV, is oxidized to compound V. A composite from several lots, weighing 0.93 g., in 20 ml. of acetone is treated at -10° C. with 2.0 ml. of Jones reagent. After stirring for 1.5 hr. the reaction mixture is quenched with isopropanol and extracted with diethyl ether. The extract is washed with brine, dried, and concentrated. The residue is subjected to silica gel chromatography, eluting with ethyl acetate (20-50%)-Skellysolve B to yield the formula-V 6-keto-PGE1, bis(tetrahydropyranyl)ether, methyl ester, 0.52 g., having Rf 0.52 (TLC on silica gel in ethyl acetate-Skellysolve B (1:1)); and infrared peaks at 1745 and 1725 cm-1 (free of OH at 3000-3500).

Aufarbeitung

  1. customthe reaction mixture is quenched with isopropanol
  2. extractionextracted with diethyl ether
  3. washThe extract is washed with brine
  4. customdried
  5. concentrationconcentrated
  6. washeluting with ethyl acetate (20-50%)-Skellysolve B

Quellen und Nachweise

ORD-Eintrag
ord-97eeed0a44514c299a7f39068ff6ad16
Quelldatensatz
uspto-grants-1980_05
Patentnummer
US04205178

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