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

HRID 65027노트

반응식

HRID 65027 반응식
[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]

참가 물질

7

반응물 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, 화합물2회

생성물 1

HCID 13687600octahydro-1-[3-((1,1-dimethylethyl)-dimethylsilyloxy)-1,5-dimethyl-5-hexenyl)-7a-methyl-1H-inden-4-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-06554e2b53b1444b8651cb6e2f241666
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04612308

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