Sodium → (2-Ethyl-6-methoxybenzofuran-3-yl)(4-hydroxyphenyl)methanone

HRID 2112289Notes

Reaction equation

HRID 2112289 reaction equation
[C:1]([C:11]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[O:13][C:12]=1[CH2:22][CH3:23])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][CH:3]=1.[Na]>CN(C)C=O>[CH2:22]([C:12]1[O:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[C:11]=1[C:1](=[O:10])[C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1)[CH3:23]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 529520473-(p-Anisoyl)-2-ethyl-6-methoxy-benzofuran

Product 1

HCID 52952247(2-Ethyl-6-methoxybenzofuran-3-yl)(4-hydroxyphenyl)methanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl formamide solution of 3-(p-anisoyl)-2-ethyl -6-methoxybenzofuran (2.39 g, 7.7 mmol) and ethanethiolic sodium salt (971 mg, 11.5 mmol) was stirred at 80° C. for 4 hours. This reaction was completed using NH4Cl solution and extraction was performed with chloroform. The extract was washed with water and saline solution, dried over Ma2SO4, and concentrated under reduced pressure. The residue was purified by HPLC (silica gel, ethyl acetate:hexane=2:8) and a target product (2.28 g, 7.70 mmol, 100%) was obtained.

Workup

  1. extractionNH4Cl solution and extraction
  2. washThe extract was washed with water and saline solution
  3. customdried over Ma2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by HPLC (silica gel, ethyl acetate:hexane=2:8)

Sources & evidence

ORD record
ord-2f1bf241bf5e4838b5b58a63a2a0d2a6
Source dataset
uspto-grants-2009_04
Patent number
US07521570B2

Reaction notes

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