Furan → 1-(Furan-2-yl)-2-(3-methoxyphenyl)ethan-1-one

HRID 1803628

Reaction equation

HRID 1803628 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:10](=[O:12])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 8029FuranHCID 9845Trifluoroacetic anhydrideHCID 15719(3-Methoxyphenyl)acetic acid

Product 1

HCID 610568711-(Furan-2-yl)-2-(3-methoxyphenyl)ethan-1-oneYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxyphenylacetic acid (20 g, 120.35 mmol) was dissolved in CH2Cl2 (200 mL), and furan (24.6 g, 361.39 mmol) and trifluoroacetic anhydride (37.8 g, 180 mmol) were added to the solution. The reaction was kept being stirred overnight at room temperature. The reaction was quenched with saturated NaHCO3 to pH=6.9, and the organic reagent in the mixture was evaporated. The residue was extracted with EtOAc, and the organic layer was washed with brine, dried over MgSO4, and evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give 1-(furan-2-yl)-2-(3-methoxyphenyl)ethan-1-one as yellow oil: 20 g (yield: 77%)

Workup

  1. customThe reaction was quenched with saturated NaHCO3 to pH=6.9
  2. customthe organic reagent in the mixture was evaporated
  3. extractionThe residue was extracted with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe resulting residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-ff791bd6ebb94de0895cb9afd7536c6e
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Linked notes

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