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

HRID 2074001Notes

Reaction equation

HRID 2074001 reaction equation
[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]

Participants

10

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 6

HCID 30318Osmium TetroxideCatalystHCID 2631-ButanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f06df5c50ee24a2c8fa824502159fc97
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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