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

HRID 1195322
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1195322
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1C1C=CC=C[NH+]=1.[Cr](Cl)([O-])(=O)=O.C([O-])(=O)C.[Na+].[CH3:28][C:29]12[CH:37]([CH:38]([CH3:50])[CH2:39][CH2:40][CH2:41][C:42]3([CH3:49])[CH2:46][O:45][C:44]([CH3:48])([CH3:47])[O:43]3)[CH2:36][CH2:35][CH:34]1[CH:33]([OH:51])[CH2:32][CH2:31][CH2:30]2.CC(O)C>C(Cl)Cl.O>[CH3:28][C:29]12[CH:37]([CH:38]([CH3:50])[CH2:39][CH2:40][CH2:41][C:42]3([CH3:49])[CH2:46][O:45][C:44]([CH3:48])([CH3:47])[O:43]3)[CH2:36][CH2:35][CH:34]1[C:33](=[O:51])[CH2:32][CH2:31][CH2:30]2
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Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 517045Sodium AcetateHCID 14180908octahydro-7a-methyl-1-[1-methyl-4-(2,2,4-trimethyl-1,3-dioxolan-4-yl) butyl]-1H-inden-4-olHCID 178526115HCID 178526115, Verbindung2×

Produkt 1

HCID 14180910octahydro-7a-methyl-1-[1-methyl-4-(2,2, 4-trimethyl-1,3-dioxolan-4-yl)-butyl]-4H-inden-4-one
Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 1.720 g of 2,2'-bipyridinium chlorochromate and 0.860 g of anhydrous sodium acetate in 10 ml of methylene chloride, was added a solution of 0.500 g of [IR-[1β(R*,S*),3aα,4β,7aβ]]-octahydro-7a-methyl-1-[1-methyl-4 -(2,2,4-trimethyl-1,3-dioxolan-4-yl) butyl]-1H-inden-4-ol in 5 ml of methylene chloride and the mixture obtained stirred at room temperature for 2 hours. Additional 0.800 g of 2,2'-bipyridinium chlorochromate was then added and the stirring continued for an additional 2.5 hours. After this time, 1 ml of 2-propanol was introduced and 15 minutes later, the mixture diluted with water and extracted with ether. The combined organic phases were dried, evaporated and the residue purified by fast filtration through silica (eluent: hexane-ethyl acetate, 3:1) to give 0.446 g (90% yield) of pure [1R-(1R*,S*)-1β,3aα,7aβ] -octahydro-7a-methyl-1-[1-methyl-4-(2,2, 4-trimethyl-1,3-dioxolan-4-yl)-butyl]-4H-inden-4-one.

Aufarbeitung

  1. customthe mixture obtained
  2. waitthe stirring continued for an additional 2.5 hours
  3. extractionextracted with ether
  4. customThe combined organic phases were dried
  5. customevaporated
  6. filtrationthe residue purified by fast filtration through silica (eluent: hexane-ethyl acetate, 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9ed7a54b43fa4e7f89113e86c175f439
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05110958

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