Methanol → HCID 57027626, compound

HRID 1728982Notes

Reaction equation

HRID 1728982 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH2:7]([C@H:9]1[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH:12]=[CH:11][CH2:10]1)C.C[OH:20]>O>[CH3:18][O:17][C:15]([C@@H:14]1[C@H:10]([CH2:9][CH3:7])[CH2:11][C:12](=[O:20])[CH2:13]1)=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 516875Potassium Permanganate2×HCID 57142067HCID 57142067, compound

Product 1

HCID 57027626HCID 57027626, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

24 g of potassium permanganate is dissolved in 15 ml of water, and 8.08 g of (1S, 6R)-6-ethyl-1-methoxycarbonylcyclohex-3-ene was added to the solution over a period of 20 minutes. The mixture was stirred for 4 hours at room temperature, and then 6 g of potassium permanganate was further added, followed by 1 hour of stirring. Methanol was added to the mixture, and the insoluble material was filtered off. Concentrated hydrochloric acid was added to the filtrate such as to adjust the pH thereof at 2, and the filtrate was extracted with a mixed solvent of ethyl acetate - tetrahydrofuran (1:1). After concentration, to the residue were added 50 ml of acetic anhydride and 2.5 g of sodium acetate, and the mixture was refluxed for 1.5 hours. The mixture was cooled down to room temperature, and a mixed solvent of hexane - ether was added thereto. The insoluble material was filtered off, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography (ether:hexane=1:2), thereby obtaining 3.99 g of titled compound.

Workup

  1. waitfollowed by 1 hour
  2. stirringof stirring
  3. filtrationthe insoluble material was filtered off
  4. additionConcentrated hydrochloric acid was added to the filtrate such as
  5. extractionat 2, and the filtrate was extracted with a mixed solvent of ethyl acetate - tetrahydrofuran (1:1)
  6. concentrationAfter concentration
  7. additionto the residue were added 50 ml of acetic anhydride and 2.5 g of sodium acetate
  8. temperaturethe mixture was refluxed for 1.5 hours
  9. temperatureThe mixture was cooled down to room temperature
  10. additiona mixed solvent of hexane - ether was added
  11. filtrationThe insoluble material was filtered off
  12. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fa5e90bba4c5407491e75d5d94f84faa
Source dataset
uspto-grants-1994_07
Patent number
US05329042

Reaction notes

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