Sodium Carbonate → (E)-ethyl 3-(4-furan-2-yl-phenyl)-but-2-enoate

HRID 984352Notes

Reaction equation

HRID 984352 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:15])=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1B(O)O>COCCOC.O>[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:15])=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 11438459(E)-ethyl 3-(4-iodophenyl)-but-2-enoate

Product 1

HCID 22557549(E)-ethyl 3-(4-furan-2-yl-phenyl)-but-2-enoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tetrakis(triphenylphoshine)palladium(0) (0.69 g, 0.60 mmol, 6 mol %) was added, under nitrogen, to a stirred solution of (E)-ethyl 3-(4-iodophenyl)-but-2-enoate (3.16 g, 10.0 mmol) in DME (100 ml), and the resulting orange coloured solution stirred at room temperature for 10 min. Aqueous 2M sodium carbonate (30.0 ml, 60.0 mmol) was then added, the mixture stirred for 10 min, then furan-2-boronic acid (2.25 g, 20.11 mmol) was added, and the reaction mixture heated to 80° C. for 20 h, under reflux. The reaction mixture was cooled, diluted with water (100 ml) and the products extracted into ethyl acetate (3×100 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the crude product, which was purified by column chromatography on silica gel (3% diethyl ether in n-heptane eluent) to give the product, (E)-ethyl 3-(4-furan-2-yl-phenyl)-but-2-enoate as an off-white solid; 2.46 g (96%).

Workup

  1. stirringthe mixture stirred for 10 min
  2. temperaturethe reaction mixture heated to 80° C. for 20 h
  3. temperatureunder reflux
  4. temperatureThe reaction mixture was cooled
  5. extractionthe products extracted into ethyl acetate (3×100 ml)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give the crude product, which
  10. customwas purified by column chromatography on silica gel (3% diethyl ether in n-heptane eluent)

Sources & evidence

ORD record
ord-5a9380a62c5e4891b429ae0f74105b64
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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