Acetic Acid → 2-(2-Furanyl)-1-phenylethanone

HRID 604474Notes

Reaction equation

HRID 604474 reaction equation
C(OC(=O)[CH:5]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)[C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.C(O)(=O)C.[Cl-].[Li+].C([O-])(O)=O.[Na+]>CN1CCCC1=O>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[CH2:5][C:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 13466307HCID 13466307, compound

Product 1

HCID 117355852-(2-Furanyl)-1-phenylethanone

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Furan-2-yl-3-oxo-3-phenyl-propionic acid ethyl ester, prepared as described by Dorsch J. B. and McElvain S. M., J Am. Chem. Soc 1932, 54, 2960-2963; (10.0 g, 39 mmol) was dissolved in N-methylpyrrolidin-2-one (13 mL) and acetic acid (3.9 mL) and lithium chloride (4.7 g, 110 mmol) was added. The reaction mixture was heated at reflux for 7 h, then saturated aqueous NaHCO3 was added and the mixture was extracted with diethyl ether. The organic extracts were dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash column chromatography using 1% ethyl acetate in hexane as eluent. Yield: 6.2 g, 85%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 7 h
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-66a53d9603c04dacab4a9eeed9853fbd
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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