Reaktion #93305

Reaktionsgleichung

2,2'-bipyridinium chlorochromate

octahydro-1-[3-((1,1-dimethylethyl)-dimethylsilyloxy)-1,5-dimethyl-5-hexenyl)-7a-methyl-1H-inden-4-ol

sodium acetate

2,2'-bipyridinium chlorochromate

isopropanol

→

octahydro-1-[3-((1,1-dimethylethyl)-dimethylsilyloxy)-1,5-dimethyl-5-hexenyl)-7a-methyl-1H-inden-4-one

Lösungsmittel

water

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred 2 hours
2. 2
   workup.STIRRINGmixture stirred for 20 minutes
3. 3
   Extraktionextracted with ether/ethyl acetate 1:1
4. 4
   WaschenThe combined organic phases were washed with water
5. 5
   Trocknenbrine, dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvents removed in vacuo
8. 8
   SonstigeThe residue was purified by silica gel chromatography
9. 9
   Wascheneluting with hexane/ethyl acetate (4:1)

Vorschrift

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.

Quelle