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Isopropanol → octahydro-7a-methyl-1-[1-methyl-4-(2, 2,4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl]-4H-inden-4-one

HRID 1195323
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1195323
[CH3:1][C:2]12[CH:10]([CH:11]([CH3:23])[CH:12]=[CH:13][CH2:14][C:15]3([CH3:22])[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]3)[CH2:9][CH2:8][CH:7]1[CH:6]([OH:24])[CH2:5][CH2:4][CH2:3]2.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1C1C=CC=C[NH+]=1.[Cr](Cl)([O-])(=O)=O.C(O)(C)C>C(Cl)Cl.O>[CH3:1][C:2]12[CH:10]([CH:11]([CH3:23])[CH:12]=[CH:13][CH2:14][C:15]3([CH3:22])[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]3)[CH2:9][CH2:8][CH:7]1[C:6](=[O:24])[CH2:5][CH2:4][CH2:3]2
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Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 517045Sodium AcetateHCID 76443847octahydro-7a-methyl-1-[1-methyl-4-(2,2,4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl]-4H-inden-4-olHCID 178526115HCID 178526115, Verbindung2×

Produkt 1

HCID 76443494octahydro-7a-methyl-1-[1-methyl-4-(2, 2,4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl]-4H-inden-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 0.145 g of [1R-(1R*,2E,S*),1β,3aα, 7aβ]-octahydro-7a-methyl-1-[1-methyl-4-(2,2,4-trimethyl-1,3-dioxolan-4-yl)-2 -butenyl)-4H-inden-4-ol in 9 ml of dry methylene chloride was treated with 0.250 g of anhydrous sodium acetate and 0.500 g of 2,2'-bipyridinium chlorochromate and the mixture stirred at room temperature for two hours. After this time, an additional 0.250 g of 2,2'-bipyridinium chlorochromate was added and the stirring compound for two more hours. After this time, 0.5 ml of isopropyl alcohol was added and the mixture stirred for 15 minutes, then diluted with water, and extracted with 3×50 ml of ether. The combined organic phases were washed with water, dried and evaporated to dryness. The crude residue obtained was purified by chromatography on silica gel, eluting with hexane-ethyl acetate (3:1) to give 0.134 g (93%) of pure [1R-(1R*,2E,S*),1β ,3aα,7aβ]-octahydro-7a-methyl-1-[1-methyl-4-(2,2, 4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl)-4H-inden-4-one, [α]D25 (c 0.2, ethanol).

Aufarbeitung

  1. stirringthe mixture stirred for 15 minutes
  2. extractionextracted with 3×50 ml of ether
  3. washThe combined organic phases were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe crude residue obtained
  7. customwas purified by chromatography on silica gel
  8. washeluting with hexane-ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-e86ccf059bbd4311816d70ad174e87d7
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05110958

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