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

HRID 1195323Notes

Reaction equation

HRID 1195323 reaction equation
[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

Participants

7

Reactant 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, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e86ccf059bbd4311816d70ad174e87d7
Source dataset
uspto-grants-1992_05
Patent number
US05110958

Reaction notes

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