Hydrochloric Acid → 2-Methyl-5-(2-nitro-vinyl)-thiophene

HRID 915652Notes

Reaction equation

HRID 915652 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[N+:9]([CH3:12])([O-:11])=[O:10].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[S:6][C:5]([CH:7]=[CH:12][N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 616635-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 539158762-Methyl-5-(2-nitro-vinyl)-thiopheneYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cool a solution of 5-methylthiophene-2-carbaldehyde (1 g, 7.9 mmol, 1 eq) and nitromethane (484 mg, 7.9 mmol, 1 eq) in methanol (3 mL) to 10° C. Add sodium hydroxide (332 mg, 8.3 mmol, 1.05 eq) as an aqueous solution (1.5 mL) to the reaction mixture. Stir reaction for 15 minutes and add ice water. Add this mixture to an aqueous HCl solution (1.67 mL concentrated HCl in 2.4 mL water) and stir overnight. Extract product with ethyl acetate, separate organics, dry with magnesium sulfate, and concentrate on rotovap to give 2-methyl-5-(2-nitrovinyl)thiophene (966 mg, 72% yield) as a crude solid.

Workup

  1. customreaction for 15 minutes
  2. stirringstir overnight
  3. customExtract product with ethyl acetate, separate organics
  4. dry with materialdry with magnesium sulfate
  5. concentrationconcentrate on rotovap

Sources & evidence

ORD record
ord-2519491042e44491b856565344cf2126
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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