Nitromethane → 1-(5-Methoxy-3-methyl-1-benzofuran-2-yl)heptan-1-one

HRID 2091226Notes

Reaction equation

HRID 2091226 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])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[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](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:8]([CH3:11])[C:7]=2[CH:12]=1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 17313Heptanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 131569985-Methoxy-3-methylbenzofuran

Product 1

HCID 667773831-(5-Methoxy-3-methyl-1-benzofuran-2-yl)heptan-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-methoxy-3-methyl-1-benzofuran (1.87 g) synthesized in Example A104(2), heptanoyl chloride (2.14 mL) and nitromethane (20 mL) was added aluminum chloride (3.07 g), and the mixture was stirred overnight at room temperature. 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 (7% ethyl acetate/hexane) to give the title object compound (2.34 g, 74%) as a pale-yellow solid.

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 (7% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23e885b65db34d2ba72faeea3e227094
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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