Water → HCID 13767629, compound

HRID 1981966Notes

Reaction equation

HRID 1981966 reaction equation
[CH3:1][CH:2]([CH:14]1[C:22]2([CH3:23])[CH:17]([CH:18]([OH:24])[CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15]1)[CH2:3][CH:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C:6]([CH3:13])([CH3:12])[CH2:5]1.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1C1C=CC=C[NH+]=1.[Cr](Cl)([O-])(=O)=O.O>C(Cl)Cl>[CH3:1][CH:2]([CH:14]1[C:22]2([CH3:23])[CH:17]([C:18](=[O:24])[CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15]1)[CH2:3][CH:4]1[O:9][C:8]([CH3:10])([CH3:11])[O:7][C:6]([CH3:13])([CH3:12])[CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 13767626HCID 13767626, compoundHCID 178526115HCID 178526115, compound2×

Product 1

HCID 13767629HCID 13767629, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.101 g of 1R-[1alpha(R*,S*),3a beta, 4beta, 7a alpha]-octahydro-1-[1-methyl-2-(2,2,4,4-tetramethyl-1,3-dioxan-6-yl)ethyl]-7a-methyl-1H-inden-4-ol in 6 mL of dry methylene chloride was treated with 0.170 g of anhydrous sodium acetate and 0.345 g of 2,2'-bipyridinium chlorochromate and the mixture stirred at room temperature for 2 hours. After this time, additional 0.150 g of 2,2'-bipyridinium chlorochromate was added and the stirring continued for 1 more hour. Water was then added to the reaction mixture which was extracted with 3×50 mL of ether. The combined organic phases were washed with water, dried and evaporated. The crude residue obtained was purified by chromatography on silica, eluting with hexane/ethyl acetate (2:1) to give 0.090 g (90% yield) of pure 1R-[1alpha(R*,S*),3a beta, 4beta, 7a alpha]-octahydro-1-[1-methyl-2-(2,2,4,4-tetramethyl- 1,3-dioxan-6-yl)ethyl]-7a-methyl-1H-inden-4-one.

Workup

  1. extractionwas extracted with 3×50 mL of ether
  2. washThe combined organic phases were washed with water
  3. customdried
  4. customevaporated
  5. customThe crude residue obtained
  6. customwas purified by chromatography on silica
  7. washeluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-50a6b34f21aa46cb9b8b4e19cb798e2d
Source dataset
uspto-grants-1986_06
Patent number
US04594432

Reaction notes

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