Hydrochloric Acid → HCID 11788723, compound

HRID 1508541Notes

Reaction equation

HRID 1508541 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.C([O:13][C:14]1[CH2:18][CH2:17][C:16](=O)[CH:15]=1)C.Cl>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:16]2[CH2:17][CH2:18][C:14](=[O:13])[CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 897773-Ethoxycyclopent-2-en-1-oneHCID 178491912HCID 178491912, compound

Product 1

HCID 11788723HCID 11788723, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 4-methoxyphenylmagnesium bromide (1M in THF) (30 ml, 30.0 mmol) was added dropwise 3-ethoxycyclopent-2-en-1-one (3.56 ml, 30.0 mmol). The reaction mixture was stirred at RT overnight. 1M aqueous hydrochloric acid and EtOAc were added. There was emulsion. The biphasic mixture was filtered through a Celite® pad. Extracted filtrate three times with EtOAc. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The Celite®/filtered solids were stirred in EtOAc/combined aqueous layers. The solids were filtered, separated filtrate layers, and extracted aqueous once more with EtOAc. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The two crude product batches were combined and purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the title compound. Mass spectrum (ESI) 189.3 (M+1).

Workup

  1. filtrationThe biphasic mixture was filtered through a Celite® pad
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. filtrationThe Celite®/filtered solids
  7. stirringwere stirred in EtOAc/
  8. filtrationThe solids were filtered
  9. customseparated filtrate layers
  10. extractionextracted aqueous once more with EtOAc
  11. washThe combined organics were washed with brine
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. customthe solvent was evaporated under reduced pressure
  15. custompurified by flash column chromatography on silica gel
  16. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-793b84fdb6664930b38c372af3b01877
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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