Methanol → methyl 5-cyano-1H-pyrrole-3-carboxylate

HRID 73656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73656
[CH3:1][O-:2].[Na+].ClC(Cl)(Cl)C([C:8]1[CH:9]=[C:10]([C:13]#[N:14])[NH:11][CH:12]=1)=O.[CH3:17][OH:18]>>[C:13]([C:10]1[NH:11][CH:12]=[C:8]([C:1]([O:18][CH3:17])=[O:2])[CH:9]=1)#[N:14]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 124151024-(trichloroacetyl)-1H-pyrrole-2-carbonitrile

Produkt 1

HCID 12415103methyl 5-cyano-1H-pyrrole-3-carboxylateAusbeute 98 %

Versuchsvorschrift

Sodium methoxide (17.8 g, 329 mmol) was added to a solution of 4-(trichloroacetyl)-1H-pyrrole-2-carbonitrile (39.0 g, 164 mmol) in methanol (350 mL). The reaction was stirred for 16 h and then the methanol was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (800 mL) and the solution was adjusted to pH 6 using 1 M hydrochloric acid. The layers were separated and then the organic layer was washed with water and brine, dried (magensium sulfate) and evaporated under reduced pressure to afford the expected product (24.2 g, 98%). 1H NMR (DMSO-d6) δ 7.76 (s, 1H), 7.28 (s, 1H), 3.72 (s, 3 H).

Aufarbeitung

  1. customthe methanol was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (800 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried (magensium sulfate)
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c56dfb14664047cbb609a367080ed4c3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829185B2

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