Nitromethane → 3-(2-Nitrovinyl)thiophene

HRID 1843828Notes

Reaction equation

HRID 1843828 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[N+:8]([CH3:11])([O-:10])=[O:9].[OH-].[Na+]>C(O)C>[N+:8]([CH:11]=[CH:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 27324183-(2-Nitrovinyl)thiopheneYield 72.28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Using an analogous reaction procedure and workup as described in Example 1, step 1, thiophene-3-carbaldehyde (3 g, 26.78 mmol) in ethanol (50 mL) was reacted with nitro methane (1.45 mL, 26.78 mmol) and 10N NaOH (3.5 mL, 28.11 mmol). The resulting mixture was stirred at 0° C. for 1.30 hours to afford 3 g of the product (72.28% yield).

Workup

  1. customan analogous reaction procedure

Sources & evidence

ORD record
ord-e2fd5b68f4b24ec5bb1bdcc3120437d3
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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