Water → 8-Formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275132노트

반응식

HRID 2275132 반응식
O.[CH3:2][C:3]1([CH3:25])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([CH:23]=C)=[CH:22][C:4]1=2.I([O-])(=O)(=O)=[O:27].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[CH:23]([C:21]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:8]4[C:13](=[CH:12][C:11]([C:16]#[N:17])=[CH:10][CH:9]=4)[NH:14][C:15]=3[C:3]([CH3:2])([CH3:25])[C:4]=2[CH:22]=1)=[O:27]

참가 물질

7

반응물 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 668340546,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

생성물 1

HCID 866638188-Formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile수율 77.9%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 6386tert-Butanol용매

실험 절차

To the THF (24 ml) and distilled water (6 ml) suspension of 6,6-dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound B2-24, 600 mg, 1.920 mmol), t-butanol solution of osmium tetraoxide (192 μl, 0.1 eq.) and sodium meta periodate (821 mg, 2.0 eq.) were added and the mixture was stirred at room temperature for 3 hr. Aqueous solution of sodium thiosulfate (0.3 M) was added to the solution, which was then extracted with an ethyl acetate. The organic layer was washed with 10% aqueous solution of disodium ethylenediamine tetraacetic acid. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (470 mg, 77%).

후처리

  1. distillationTo the THF (24 ml) and distilled
  2. additionwere added
  3. extractionwas then extracted with an ethyl acetate
  4. washThe organic layer was washed with 10% aqueous solution of disodium ethylenediamine tetraacetic acid
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe residues obtained
  8. concentrationafter concentration under reduced pressure
  9. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-980218174eaa4a708c2789467bc117f8
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126931B2

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