Methyl Benzoate → 1-(1-Methylpyrrol-2-yl)-3-phenyl-1,3-propanedione

HRID 892428Notes

Reaction equation

HRID 892428 reaction equation
CCCCCC.[H-].[Na+].[C:9]([O:17]C)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:19]([C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)(=[O:21])[CH3:20]>C(OCC)C.C(O)C.O>[CH3:27][N:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:19](=[O:21])[CH2:20][C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:17]

Participants

8

Reactant 4

HCID 7150Methyl BenzoateHCID 8058HexaneHCID 24758Sodium hydrideHCID 612402-Acetyl-1-methylpyrrole

Product 1

HCID 198953681-(1-Methylpyrrol-2-yl)-3-phenyl-1,3-propanedioneYield 17.6%

Reagents, catalysts & solvents 3

HCID 702EthanolCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred, cooled (5° C.) slurry of 0.96 g (0.04 mol) of hexane-washed sodium hydride in 2.72 g (0.02 mol) of methyl benzoate under nitrogen was added a solution of 5.0 g (0.04 mol) of 2-acetyl-1-methylpyrrole in 30 mL of ethyl ether. A few drops of ethanol were added. The reaction mixture was allowed to stir at 5° C. for 12 h. The mixture was poured into water and extracted with ethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, and filtered. Removal of solvents gave a waxy solid which was purified by flash-chromatography (silica gel, ethyl acetate/hexane as eluent) to give 0.8 g of 1-(1-methylpyrrol-2-yl)-3-phenyl-1,3-propanedione.

Workup

  1. extractionextracted with ethyl ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customRemoval of solvents
  6. customgave a waxy solid which
  7. customwas purified by flash-chromatography (silica gel, ethyl acetate/hexane as eluent)

Sources & evidence

ORD record
ord-0926807333e54a9b8dfffe095356c02c
Source dataset
uspto-grants-1992_06
Patent number
US05118681

Reaction notes

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