Isopropanol → HCID 13687600, compound

HRID 65027Notes

Reaction equation

HRID 65027 reaction equation
[CH3:1][C:2]([Si:5]([CH3:27])([CH3:26])[O:6][CH:7]([CH2:22][C:23]([CH3:25])=[CH2:24])[CH2:8][CH:9]([CH:11]1[C:19]2([CH3:20])[CH:14]([CH:15]([OH:21])[CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12]1)[CH3:10])([CH3:4])[CH3:3].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]([Si:5]([CH3:26])([CH3:27])[O:6][CH:7]([CH2:22][C:23]([CH3:25])=[CH2:24])[CH2:8][CH:9]([CH:11]1[C:19]2([CH3:20])[CH:14]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12]1)[CH3:10])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 517045Sodium AcetateHCID 13687598octahydro-1-[3-((1,1-dimethylethyl)-dimethylsilyloxy)-1,5-dimethyl-5-hexenyl)-7a-methyl-1H-inden-4-olHCID 178526115HCID 178526115, compound2×

Product 1

HCID 13687600HCID 13687600, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.24 g of [1R-[1alpha(R*,S*)-3abeta,4abeta,7aalpha]]-octahydro-1-[3-((1,1-dimethylethyl)-dimethylsilyloxy)-1,5-dimethyl-5-hexenyl)-7a-methyl-1H-inden-4-ol in 15 ml of dry methylene chloride was treated with 0.35 g of anhydrous sodium acetate and 0.71 g of 2,2'-bipyridinium chlorochromate and the mixture stirred at room temperature for 3 hours. After this time an additional 0.355 g of 2,2'-bipyridinium chlorochromate was added. The mixture was stirred 2 hours then 1 ml of isopropanol was added, mixture stirred for 20 minutes then diluted with water and extracted with ether/ethyl acetate 1:1. The combined organic phases were washed with water, then brine, dried over anhydrous sodium sulfate, filtered and the solvents removed in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (4:1) to give 0.238 g of pure [1R-[1alpha(R*,S*)-3abeta,7aalpha]]octahydro-1-[3-((1,1-dimethylethyl)-dimethylsilyloxy)-1,5-dimethyl-5-hexenyl)-7a-methyl-1H-inden-4-one.

Workup

  1. stirringThe mixture was stirred 2 hours
  2. stirringmixture stirred for 20 minutes
  3. extractionextracted with ether/ethyl acetate 1:1
  4. washThe combined organic phases were washed with water
  5. dry with materialbrine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvents removed in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-06554e2b53b1444b8651cb6e2f241666
Source dataset
uspto-grants-1986_09
Patent number
US04612308

Reaction notes

Loading…