Tetrahydrofuran → 4-(3-Methoxyphenyl)-2,5-dihydrofuran-2-one

HRID 8192Notes

Reaction equation

HRID 8192 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[C:12](=[O:15])([O-])[O-:13].[Na+].[Na+].O1C[CH2:21][CH2:20][CH2:19]1>O.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]2[CH2:21][O:13][C:12](=[O:15])[CH:19]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 232433284-(3-Methoxyphenyl)-2,5-dihydrofuran-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

3-Methoxy-phenyl-boronic acid (2.16 g, 14.2 mmol) and trifluoromethansulfonic acid 5-oxo-2,5-dihydro-furan-3-yl ester1 (3 g, 12.92 mmol) in tetrahydrofuran (110 mL) is dissolved and de-gassed for 15 min. To this solution is added sodium carbonate (3.42 g, 32.3 mmol) in water (10 mL) and tetrakis-triphenylphosphine-palladium(0) (0.75 g, 0.646 mmol). The reaction mixture is refluxed for 45 min, cooled to room temperature, diluted with ether (50 mL) and filtered through a Celite® pad. The filtrate is washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (3:7 ethyl acetate/hexanes) to yield the title compound, 1.9 g (71%), as a white crystalline solid.

Workup

  1. customde-gassed for 15 min
  2. temperatureThe reaction mixture is refluxed for 45 min
  3. filtrationfiltered through a Celite® pad
  4. washThe filtrate is washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on SiO2 (3:7 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6312909cd6b54e469cf5f87a6f5c5ccc
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

Loading…