HCID 66868360, compound → HCID 66867027, compound

HRID 1631894Notes

Reaction equation

HRID 1631894 reaction equation
[CH:1]1([CH:4]=[C:5]2[C:9](=[O:10])[C:8]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:7]([O:20]C)[CH2:6]2)[CH2:3][CH2:2]1>N1CCOCC1>[CH:1]1([CH:4]=[C:5]2[CH2:6][C:7](=[O:20])[CH:8]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:9]2=[O:10])[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 66868360HCID 66868360, compound

Product 1

HCID 66867027HCID 66867027, compoundYield 266.2%

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

Procedure

A solution of 5-[1-Cyclopropyl-methylidene]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (83 mg, 0.28 mmol) in morpholine (3 ml) was heated at 10° C. for 17 hours. The reaction was allowed to cool to room temperature and then evaporated to dryness under reduced pressure. The crude material was dissolved in EtOAc (15 ml) and then washed with 2M HCl (3×15 ml) and brine (15 ml). The organic phase was dried over Na2SO4, filtered and evaporated to dryness under reduced pressure to give a colourless oil (200 mg). The crude material was purified by flash chromatography over SiO2 using a 100% hexane to 100% EtOAc gradient to give the desired compound as a white solid (45 mg).

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe crude material was dissolved in EtOAc (15 ml)
  3. washwashed with 2M HCl (3×15 ml) and brine (15 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-45bb9af27cee481889894666949212aa
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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