Nitromethane → Cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methanone

HRID 2091429Notes

Reaction equation

HRID 2091429 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.[CH:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH:13]1([C:19]([C:7]2[C:6]3[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[O:9][C:8]=2[CH3:10])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 75938Cyclohexanecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 130130736-Methoxy-2-methylbenzofuran

Product 1

HCID 66778158Cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methanoneYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6-methoxy-2-methyl-1-benzofuran (1.50 g), cyclohexanecarbonyl chloride (1.36 mL) and nitromethane (15 mL) was added aluminum chloride (1.85 g) at 0° C., and the mixture was stirred for 1 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 (0-10% ethyl acetate/hexane) to give the title object compound (1.18 g, 47%) 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 (0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2e1d509d621f4d1d9635951cfb3a5140
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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