반응 #93305

반응 방정식

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

용매

water

methylene chloride

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred 2 hours
2. 2
   workup.STIRRINGmixture stirred for 20 minutes
3. 3
   추출extracted with ether/ethyl acetate 1:1
4. 4
   세척The combined organic phases were washed with water
5. 5
   건조brine, dried over anhydrous sodium sulfate
6. 6
   여과filtered
7. 7
   기타the solvents removed in vacuo
8. 8
   기타The residue was purified by silica gel chromatography
9. 9
   세척eluting with hexane/ethyl acetate (4:1)

실험 절차

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.

출처