Dicyclopentadiene → 3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoindene-5,6-diol

HRID 1727192

반응식

HRID 1727192 반응식
[CH:1]12[CH2:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[CH:2]2[CH:3]=[CH:4][CH2:5]1.[OH2:11].[OH2:12].C[N+]([O-])(C)C.[O-][Si]([O-])=O.[Mg+2].S([O-])(O)=O.[Na+]>ClCCl.C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.[Os](=O)(=O)(=O)=O.N1C=CC=CC=1.CC(C)=O.O>[CH:1]12[CH2:10][CH:7]([CH:8]([OH:12])[CH:9]1[OH:11])[CH:6]1[CH:2]2[CH:3]=[CH:4][CH2:5]1

참가 물질

11

반응물 4

HCID 6492DicyclopentadieneHCID 61680MAGNESIUM SILICATE (synthetic)HCID 198430Trimethylamine oxide dihydrateHCID 23665763Sodium Bisulfite

생성물 1

HCID 131669763a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoindene-5,6-diol수율 19.6%

시약·촉매·용매 6

HCID 30318Osmium Tetroxide촉매2회HCID 82707Tetrabutylammonium Acetate촉매HCID 180Acetone용매HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

A slurry of tricyclo[5.2.1.02,6]deca-3,8-diene (26.5 g, 0.2 mol), trimethylamine N-oxide dihydrate (22.3 g, 0.2 mol) and osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, 2 □l) in dichloromethane (200 ml) was stirred for 18 h. A further portion of osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, ca. 2 □l) was added, water (25 ml) and acetone (50 ml) was added and the reaction mixture was stirred for a further 72 h. Pyridine (0.5 ml) and tetrabutylammonium acetate (0.5 g) were added. Florisil (10 g) and aqueous sodium hydrogensulfite solution was added and the reaction mixture was stirred for 20 min. The reaction mixture was filtered and the product was extracted with dichloromethane (3 times). The combined organic extracts were washed with water, brine and then concentrated to give an oil. The crude oil was purified by flash chromatography eluting with ethyl acetate:hexane (10:90) and then ethyl acetate, to give a waxy solid (6.5 g, 19%).

후처리

  1. stirringthe reaction mixture was stirred for 20 min
  2. filtrationThe reaction mixture was filtered
  3. extractionthe product was extracted with dichloromethane (3 times)
  4. washThe combined organic extracts were washed with water, brine
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude oil was purified by flash chromatography
  8. washeluting with ethyl acetate:hexane (10:90)

출처 및 근거

ORD 기록
ord-73906d6b0952423691dcef7cb06941fe
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07494992B2

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