Nitromethane → 5-Chloro-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one

HRID 2091232Notes

Reaction equation

HRID 2091232 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.[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19].[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12][C:7]=2[C:8]=1[CH3:11])=[O:19]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 740895-Chlorovaleryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 131569985-Methoxy-3-methylbenzofuran

Product 1

HCID 667781595-Chloro-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-oneYield 76%

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) above, 5-chlorovaleryl chloride (1.74 mL) and nitromethane (40 mL) was added aluminum chloride (2.47 g) at 0° C., and the mixture was stirred 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 (5% ethyl acetate/hexane) to give the title object compound (2.63 g, 76%) 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 (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d015985c2ecb4af3a5cb8ac7e6b694c4
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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