Ethanol → 5-ethenyl-2-benzofuran-1(3H)-one

HRID 2175758Notes

Reaction equation

HRID 2175758 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2.[CH2:12](O)[CH3:13]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:12]([C:2]1[CH:11]=[CH:10][C:9]2[C:7](=[O:8])[O:6][CH2:5][C:4]=2[CH:3]=1)=[CH2:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 6031445-Bromophthalide

Product 1

HCID 211063135-ethenyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

5-Bromophthalide (50 g, 235 mmol), potassium vinyl trifluoroborate (62.9 g, 469 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (9.58 g, 11.7 mmol) were added to ethanol (500 mL) then TEA (65.4 mL, 469 mmol) was added. The reaction mixture was degassed then heated at reflux for 8 h. The reaction was worked up by diluting with ethyl acetate and washing with brine twice. The organic layer was dried and evaporated to dryness. The crude product was purified by MPLC (silica, 600 g column) with 25% EtOAc/hexane (3 L) then with 30% EtOAc/Hexane (2 L) to yield the title compound.

Workup

  1. customThe reaction mixture was degassed
  2. temperaturethen heated
  3. temperatureat reflux for 8 h
  4. additionby diluting with ethyl acetate
  5. washwashing with brine twice
  6. customThe organic layer was dried
  7. customevaporated to dryness
  8. customThe crude product was purified by MPLC (silica, 600 g column) with 25% EtOAc/hexane (3 L)

Sources & evidence

ORD record
ord-d01f189fd38b4de18386370736259cba
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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