Triethylamine → 1-(7-Ethyl-1-benzofuran-2-yl)ethan-1-one

HRID 1282827Notes

Reaction equation

HRID 1282827 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([CH2:13][CH3:14])=[CH:11][C:10](Br)=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].C(N(CC)CC)C>CO.[Pd]>[C:1]([C:4]1[O:5][C:6]2[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 877851-(5-Bromo-7-ethyl-1-benzofuran-2-yl)ethan-1-one

Product 1

HCID 124484571-(7-Ethyl-1-benzofuran-2-yl)ethan-1-oneYield 86.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 80.1 g of 2-acetyl-5-bromo-7-ethylbenzofuran, 37.5 g of triethylamine and 5 g of 5% palladium-on-carbon in 1300 ml of methanol was hydrogenated at room temperature and atmospheric pressure until 1 molar equivalent of hydrogen had been absorbed. The catalyst was filtered off and the filtrate evaporated to dryness. The residual solid was dissolved in ethyl acetate, the resulting solution washed with water and with brine and dried over anhydrous sodium sulphate. The sodium sulphate was then filtered off and the filtrate evaporated under reduced pressure. The residual solid was crystallized from petroleum ether (boiling range 60°-80°C) to give 48.7 g of 2-acetyl-7-ethylbenzofuran as a white crystalline solid of melting point 59°-60°C.

Workup

  1. customwas hydrogenated at room temperature
  2. customatmospheric pressure until 1 molar equivalent of hydrogen had been absorbed
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate evaporated to dryness
  5. dissolutionThe residual solid was dissolved in ethyl acetate
  6. washthe resulting solution washed with water and with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationThe sodium sulphate was then filtered off
  9. customthe filtrate evaporated under reduced pressure
  10. customThe residual solid was crystallized from petroleum ether (boiling range 60°-80°C)

Sources & evidence

ORD record
ord-0b3fab9fba2a4a559cedf27d778ad6f8
Source dataset
uspto-grants-1976_08
Patent number
US03972900

Reaction notes

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