Sodium Hydroxide → HCID 68547711, compound

HRID 1516596Notes

Reaction equation

HRID 1516596 reaction equation
[CH:1]([C:3]1[O:7][C:6]([N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([C:19]#[N:20])=[CH:9]2)=[CH:5][CH:4]=1)=[O:2].[OH-:21].[Na+]>O1CCCC1.[Ag]=O>[C:19]([C:10]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:12][N:8]([C:6]2[O:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][CH:5]=2)[CH:9]=1)#[N:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 87474700HCID 87474700, compound

Product 1

HCID 68547711HCID 68547711, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-formylfuran-2-yl)-4-phenyl-1H-pyrrole-3-carbonitrile (0.14 g) in tetrahydrofuran (4 mL) were added silver oxide (0.15 g) and sodium hydroxide aqueous solution (2 mol/L, 0.4 mL), and this mixture was stirred at room temperature for 6 hours. The insoluble material was removed by filtration, and this filtrate was concentrated. To this residue were added water (15 mL) and hydrochloric acid (2 mol/L, 2 mL), this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. This residue was purified by column chromatography on silica gel (eluent: methanol/dichloromethane=1/10−1/5) to give the title compound (0.040 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthis filtrate was concentrated
  3. additionTo this residue were added water (15 mL) and hydrochloric acid (2 mol/L, 2 mL)
  4. extractionthis mixture was extracted with ethyl acetate
  5. washThis organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThis residue was purified by column chromatography on silica gel (eluent: methanol/dichloromethane=1/10−1/5)

Sources & evidence

ORD record
ord-8c464e05091b4712a66bb3bc6f87e426
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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