Tetrahydrofuran → HCID 18470693, compound

HRID 2228624Notes

Reaction equation

HRID 2228624 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[NH:6][C:5]=1[CH3:16])(=[O:3])[CH3:2].C1C[O:20]CC1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[OH-].[Na+]>O.C(O)(=O)C>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[NH:6][C:5]=1[CH:16]=[O:20])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 9869224Ammonium cerium (IV) nitrateHCID 18470723HCID 18470723, compound

Product 1

HCID 18470693HCID 18470693, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-Acetyl-2,4-dimethyl-5-(4-pyridyl)-1H-pyrrole (800 mg, 3.74 mmol) was dissolved with THF (37 mL), acetic acid (45 mL) and water (37 mL). Ammonium cerium(IV) nitrate (8.38 g, 15.3 mmol) was added to the mixture at room temperature and stirred for 1.5 hours. The mixture was neutralized with 2 M aqueous NaOH solution and extracted with ethyl acetate (150 mL×3). The combined organic layers were washed with brine, dried over MgSO4, and evaporated in vacio. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (2:1) to afford the title compound (190 mg, 22% yield) as a solid.

Workup

  1. extractionextracted with ethyl acetate (150 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacio
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate-hexane (2:1)

Sources & evidence

ORD record
ord-4d2e531a7118461cbe5fa1c10a459e13
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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