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

HRID 1848405Notes

Reaction equation

HRID 1848405 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]>>[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

3

Reactant 2

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

Product 1

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

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)-CH2Cl2Adduct (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 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

Sources & evidence

ORD record
ord-c2f11bd3c67f4f28b06ae07d8fdf9d9e
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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