HCID 67551207, compound → HCID 69844816, compound

HRID 1860270Notes

Reaction equation

HRID 1860270 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[CH:6][C:7]1[S:8][C:9]([N+:18]([O-])=O)=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1)[CH3:2]>O1CCOCC1.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[CH:6][C:7]1[S:8][C:9]([NH2:18])=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67551207HCID 67551207, compound

Product 1

HCID 69844816HCID 69844816, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ethyl-4-[(ethoxycarbonyl)methyl]-5-nitro-2-thiopheneacrylate (230 mg, 0.74 mmol) was dissolved in aqueous dioxan (6 ml, 5:1 dioxan/water) and treated with reduced iron powder (0.4 g, 7.2 mmol) and iron sulfate heptahydrate (50 mg, 0.18 mmol). The reaction mixture was refluxed for 1 hour then filtered through celite and washed through with diethyl ether. The combined organics were then washed with saturated sodium hydrogen carbonate, saturated sodium chloride, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel using hexane/ethyl acetate (2:1) as eluent to give 150 mg 3-(5-amino-4-ethoxycarbonylmethyl-thiophen-2-yl)-acrylic acid ethyl ester. MS(ES): m/e 284 [M+H].

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. filtrationthen filtered through celite
  3. washwashed through with diethyl ether
  4. washThe combined organics were then washed with saturated sodium hydrogen carbonate, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-7483aa1ce40c4dc48579a9c9bc5cd0b9
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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