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Isopropanol → octahydro-7a-methyl-1-[1-methyl-4-(2, 2,4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl]-4H-inden-4-one

HRID 1195323
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HRID 1195323 반응식
[CH3:1][C:2]12[CH:10]([CH:11]([CH3:23])[CH:12]=[CH:13][CH2:14][C:15]3([CH3:22])[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]3)[CH2:9][CH2:8][CH:7]1[CH:6]([OH:24])[CH2:5][CH2:4][CH2:3]2.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]12[CH:10]([CH:11]([CH3:23])[CH:12]=[CH:13][CH2:14][C:15]3([CH3:22])[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]3)[CH2:9][CH2:8][CH:7]1[C:6](=[O:24])[CH2:5][CH2:4][CH2:3]2
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참가 물질

7

반응물 4

HCID 3776IsopropanolHCID 517045Sodium AcetateHCID 76443847octahydro-7a-methyl-1-[1-methyl-4-(2,2,4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl]-4H-inden-4-olHCID 178526115HCID 178526115, 화합물2회

생성물 1

HCID 76443494octahydro-7a-methyl-1-[1-methyl-4-(2, 2,4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl]-4H-inden-4-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 0.145 g of [1R-(1R*,2E,S*),1β,3aα, 7aβ]-octahydro-7a-methyl-1-[1-methyl-4-(2,2,4-trimethyl-1,3-dioxolan-4-yl)-2 -butenyl)-4H-inden-4-ol in 9 ml of dry methylene chloride was treated with 0.250 g of anhydrous sodium acetate and 0.500 g of 2,2'-bipyridinium chlorochromate and the mixture stirred at room temperature for two hours. After this time, an additional 0.250 g of 2,2'-bipyridinium chlorochromate was added and the stirring compound for two more hours. After this time, 0.5 ml of isopropyl alcohol was added and the mixture stirred for 15 minutes, then diluted with water, and extracted with 3×50 ml of ether. The combined organic phases were washed with water, dried and evaporated to dryness. The crude residue obtained was purified by chromatography on silica gel, eluting with hexane-ethyl acetate (3:1) to give 0.134 g (93%) of pure [1R-(1R*,2E,S*),1β ,3aα,7aβ]-octahydro-7a-methyl-1-[1-methyl-4-(2,2, 4-trimethyl-1,3-dioxolan-4-yl)-2-butenyl)-4H-inden-4-one, [α]D25 (c 0.2, ethanol).

후처리

  1. stirringthe mixture stirred for 15 minutes
  2. extractionextracted with 3×50 ml of ether
  3. washThe combined organic phases were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe crude residue obtained
  7. customwas purified by chromatography on silica gel
  8. washeluting with hexane-ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-e86ccf059bbd4311816d70ad174e87d7
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05110958

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