Acetone → HCID 53445980, compound

HRID 1281736Notes

Reaction equation

HRID 1281736 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.CC(C)=[O:13].[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[C:16]1[C:24](=O)[CH3:25]>C1(C)C=CC=CC=1.O.C(O)(=O)C>[CH2:8]([O:7][C:3](=[O:10])[CH:24]([C:16]1[O:15][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=1)[CH:25]=[O:13])[CH3:9]

Participants

8

Reactant 4

HCID 180AcetoneHCID 7766Diethyl CarbonateHCID 154352-AcetylbenzofuranHCID 24758Sodium hydride

Product 1

HCID 53445980HCID 53445980, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a vigorously stirred suspension of NaH (60% dispersion in mineral oil, 2.6 g, 65 mmol, 3.32 equiv.) and diethyl carbonate (4.7 mL, 38.83 mmol, 1.99 equiv.) in dry toluene (30 mL) was added drop wise (over a period of 1 h) a solution of the methyl ketone, 1-benzofuran-2-yl-ethanone (1 g, 7.87 mmol) in toluene (5 mL) under reflux. After addition, the mixture was stirred at reflux for 0.5 h. The mixture was cooled to RT and was acidified with glacial acetic acid. After adding cold water, the mixture was extracted 3 times with ethyl acetate. Combined organic extract was washed with water and brine. After drying over MgSO4, solvent was evaporated to furnish the crude βketoester, 3-benzofuran-2-yl-3-oxo-propionic acid ethyl ester. To the crude product was added absolute ethanol (10 mL) and hydrazine hydrate (1.5 mL, excess). The mixture was kept under reflux for 4 h. A solid separated, which was filtered and washed with EtOH. Upon drying, a 1.87 g (48%) of the pyrazolone (VId) was isolated. 1H-NMR (DMSO-d6) δ 12.5 (br s, 1H), 10.1 (br s, 1H), 7.62-7.18 (series of multiplets, 4H), 7.10 (s, 1H), 5.87 (s, 1H). MS: 201(M+H)

Workup

  1. temperatureunder reflux
  2. additionAfter addition
  3. temperatureat reflux for 0.5 h
  4. extractionthe mixture was extracted 3 times with ethyl acetate
  5. extractionCombined organic extract
  6. washwas washed with water and brine
  7. dry with materialAfter drying over MgSO4, solvent
  8. customwas evaporated

Sources & evidence

ORD record
ord-e4c5efc1617849249ed9b69a398a95a2
Source dataset
uspto-grants-2002_09
Patent number
US06455525B1

Reaction notes

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