Ethyl Acetate → 2-(5-Ethylthiophen-2-yl)-4-methoxybenzo(b)furan

HRID 2085180Notes

Reaction equation

HRID 2085180 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([Sn](C)(C)C)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Br[C:17]1[S:18][C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=1.C(OCC)(=O)C>C1COCC1>[CH2:22]([C:19]1[S:18][C:17]([C:9]2[O:8][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=3[CH:10]=2)=[CH:21][CH:20]=1)[CH3:23]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 227291122-Bromo-5-ethylthiopheneHCID 227291264-Methoxy-2-(trimethylstannyl)benzo(b)furan

Product 1

HCID 227293132-(5-Ethylthiophen-2-yl)-4-methoxybenzo(b)furanYield 41.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxy-2-(trimethylstannyl)-benzo(b)furan (3.00 g) and 2-bromo-5-ethylthiophene (1.84 g) in THF (25 ml) was added bistriphenylphosphinepalladium dichloride (224 mg), and the mixture was stirred with refluxing overnight. After cooling, ethyl acetate was added to the reaction mixture and the mixture was filtered through celite. The filtrate was washed with water and saturated brine, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.04 g) as a yellow oil.

Workup

  1. temperaturewith refluxing overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through celite
  4. washThe filtrate was washed with water and saturated brine
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-478d0947a1614d819b9a117dd41938e8
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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