Acetic Acid → HCID 73197186, compound

HRID 636727Notes

Reaction equation

HRID 636727 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH3:8][C:9]([N+:12]([O-])=[O:13])([CH3:11])[CH3:10].C(O)(=O)C>C(O)C.[Zn]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[N+:12]([C:9]([CH3:11])([CH3:10])[CH3:8])[O-:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 116722-Methyl-2-nitropropane

Product 1

HCID 73197186HCID 73197186, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a suspension of thiophene-2-carbaldehyde (296.7 mg, 2.65 mmol), 1,1-dimethylnitroethane (542.9 mg, 5.27 mmol) and zinc (516.3 mg, 7.90 mmol) in ethanol (3.0 ml) was added acetic acid (946.6 mg, 15.8 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for one day. Zinc acetate in the mixture was filtered off and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=1/2).

Workup

  1. stirringThe mixture was stirred at room temperature for one day
  2. filtrationZinc acetate in the mixture was filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-240656e2ade84b6692051af393a12ac7
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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