Réaction #93305

Équation de réaction

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

Solvants

water

methylene chloride

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source