Furan → 1-(Furan-2-yl)-2-(4-methoxyphenyl)ethan-1-one

HRID 2372364Notes

Reaction equation

HRID 2372364 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](Cl)=[O:16])=[CH:10][CH:9]=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:15](=[O:16])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8029FuranHCID 62406Trifluoromethanesulfonic acidHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 134271661-(Furan-2-yl)-2-(4-methoxyphenyl)ethan-1-oneYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Furan (5 g, 73.5 mmol) in CH2Cl2 (10 ml) was added to a solution of p-methoxyphenylacetyl chloride (2.21 g, 14.7 mmol) and trifluoromethanesulfonic acid (150 μl) in CH2Cl2 (25 ml) at reflux. The reaction was quenched after 3 hours by pouring the solution over a 10% HCl/ice slurry. The organic layer was washed with 10% aqueous NaOH, dried over MgSO4, and the solvent was removed under reduced pressure. The crude oil was chromatographed ion SiO2 (85 g), eluting with Hexane/EtOAc, 4/1, to give 20 (1.12 g, 35.3%) 41.5°-43.0° C.

Workup

  1. temperatureat reflux
  2. customThe reaction was quenched after 3 hours
  3. additionby pouring the solution over a 10% HCl/ice slurry
  4. washThe organic layer was washed with 10% aqueous NaOH
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe crude oil was chromatographed ion SiO2 (85 g)
  8. washeluting with Hexane/EtOAc, 4/1

Sources & evidence

ORD record
ord-074f22c9675343ff8a0c942d034522f6
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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