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

HRID 65027ノート

反応式

HRID 65027 の反応式
[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]

参加物

7

反応物 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、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-06554e2b53b1444b8651cb6e2f241666
出典データセット
uspto-grants-1986_09
特許番号
US04612308

反応ノート

読み込み中…