Nitromethane → HCID 15696516, compound

HRID 2371035Notes

Reaction equation

HRID 2371035 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2]1.[CH3:13][N+:14]([O-:16])=[O:15]>>[N+:14]([CH2:13][CH:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 6375NitromethaneHCID 669147533-Thiophen-3-yl-acrylic acid ethyl ester

Product 1

HCID 15696516HCID 15696516, compoundYield 65%

Procedure

To a solution of ethyl 3-(thiophen-3-yl)acrylate (5 g, 27.5 mmol) in CH3NO2 (20 mL) was added Triton B (5 mL) under N2 and the resulting reaction mixture was refluxed overnight. The reaction mixture was concentrated and then diluted with water. The mixture was extracted with EtOAc, washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (4.3 g, 65%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with water
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationAfter filtration and concentration
  9. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f4c3f778f76746779cbb1d5f13b1b61f
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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