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

HRID 892784Notes

Reaction equation

HRID 892784 reaction equation
[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

Participants

7

Reactant 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, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

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 [1R-[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.

Workup

  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)

Sources & evidence

ORD record
ord-1ec3f2d2a2c74d4697fd5bf75eefe42d
Source dataset
uspto-grants-1992_06
Patent number
US05120722

Reaction notes

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