Nitromethane → (5-Methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methanone

HRID 2091212Notes

Reaction equation

HRID 2091212 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[C:8]([CH3:11])[C:7]=2[CH:12]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:20])=[C:8]([CH3:11])[C:7]=2[CH:12]=1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 131569985-Methoxy-3-methylbenzofuran

Product 1

HCID 1473421(5-Methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methanoneYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-methoxy-3-methyl-1-benzofuran (2.00 g) synthesized in Example A104(2), benzoyl chloride (1.68 mL) and nitromethane (20 mL) was added aluminum chloride (3.28 g), and the mixture was stirred at room temperature for 2 hr. Water was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) and further by silica gel column chromatography (20% ethyl acetate/hexane) to give the title object compound (2.03 g, 62%) as a yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) and further by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-efc693a31d8e4f988e8f164f7f88f8c0
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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