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

HRID 1465758Notes

Reaction equation

HRID 1465758 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 (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmol), PdCl2(dppf)-CH2Cl2 Adduct (182 mg, 0.223 mmol), and TEA (0.622 mL, 4.47 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 min. 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 using a 120 g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield the title product. LC-MS: M+1=175 at 2.42 retention time.

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

Sources & evidence

ORD record
ord-6c5da85a27a44dfe9d4d47304afea0c4
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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