Ethanol → 4-methyl-5-vinylisobenzofuran-1(3H)-one

HRID 2281283Notes

Reaction equation

HRID 2281283 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH3:12].[CH2:13](O)[CH3:14]>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:13]([C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH3:12])=[CH2:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 595687115-Bromo-4-methylisobenzofuran-1(3H)-one

Product 1

HCID 666439224-methyl-5-vinylisobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

5-Bromo-4-methyl-2-benzofuran-1(3H)-one (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140° C. for 20 minutes. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz, CDCl3): δ ppm 7.76 (d, J=8 Hz, 1H), 7.03 (dd, J=11, 17 Hz, 1H), 5.84 (d, J=17 Hz, 1H), 5.55 (d, J=11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+1]=175.

Workup

  1. customThe tube was sealed
  2. customdegassed
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washwashed with brine twice
  5. customdried
  6. customevaporated to dryness
  7. customThe crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solvent system)

Sources & evidence

ORD record
ord-b30910808948456985b52f49072e2a62
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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