Nitromethane → Cyclopentyl(3-methyl-1-benzothiophen-2-yl)methanone

HRID 2091077Notes

Reaction equation

HRID 2091077 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[CH:11]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1.[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH:11]1([C:16]([C:3]2[S:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[CH3:1])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 738173-Methylbenzo[b]thiopheneHCID 78284Cyclopentanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66777325Cyclopentyl(3-methyl-1-benzothiophen-2-yl)methanoneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-methyl-1-benzothiophene (1.00 g), cyclopentanecarbonyl chloride (903 μL) and nitromethane (10 mL) was added aluminum chloride (1.35 g) at 0° C., and the mixture was stirred for 1.5 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 NH-silica gel column chromatography (ethyl acetate) to give the title object compound (1.54 g, 93%) as a pale-brown 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 NH-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-094a25237d9f46af911b80f9f544d56f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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