Cyclohexene → 1-Acetyl-5-carbomethoxy-7-chloro-4-methoxyindole

HRID 2074001노트

반응식

HRID 2074001 반응식
[CH2:1]([C:4]1[C:5]([O:19][CH3:20])=[C:6]([CH:11]=[C:12]([Cl:18])[C:13]=1[NH:14][C:15](=[O:17])[CH3:16])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=C.I([O-])(=O)(=O)=O.[Na+].C1CCCCC=1>C(O)CCC.O.O1CCOCC1.O.C(O)(C(F)(F)F)=O.C(Cl)Cl.[Os](=O)(=O)(=O)=O>[C:15]([N:14]1[C:13]2[C:4](=[C:5]([O:19][CH3:20])[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][C:12]=2[Cl:18])[CH:1]=[CH:2]1)(=[O:17])[CH3:16]

참가 물질

10

반응물 3

HCID 8079CyclohexeneHCID 10709158Methyl 4-acetamido-3-allyl-5-chloro-2-methoxybenzoateHCID 23667635Sodium periodate

생성물 1

HCID 104931031-Acetyl-5-carbomethoxy-7-chloro-4-methoxyindole

시약·촉매·용매 6

HCID 30318Osmium Tetroxide촉매HCID 2631-Butanol용매HCID 962Water용매HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

A 2.5% solution of osmium tetroxide in butanol (0.25 ml) is added to a stirred solution of the methoxy compound from step 7 above (1.5 g) in H2O-dioxane (15 ml/45 ml) and stirred for 30 minutes. Sodium periodate (2.25 g) is added portionwise over one hour and the reaction mixture stirred for 31/2 hours. Cyclohexene (1 ml) is added, the mixture stirred for one hour, diluted with H2O and extracted with CHCl3. The organic layer is separated, dried (MgSO4) and evaporated affording a gum which is dissolved in TFA and allowed to stand for 15 minutes. The acid solution is diluted to 100 mls with CH2Cl2 and washed with H2O, saturated NaHCO3, dried (MgSO4) and evaporated affording a solid which is chromatographed on silica gel affording a colorless solid which is the indole as confirmed by NMR (270 MHz, CDCl2).

후처리

  1. stirringthe reaction mixture stirred for 31/2 hours
  2. stirringthe mixture stirred for one hour
  3. extractionextracted with CHCl3
  4. customThe organic layer is separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customaffording a gum which
  8. waitto stand for 15 minutes
  9. washwashed with H2O, saturated NaHCO3
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customaffording a solid which
  13. customis chromatographed on silica gel affording a colorless solid which

출처 및 근거

ORD 기록
ord-f06df5c50ee24a2c8fa824502159fc97
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04920219

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