Lithium Hydroxide → 3-Chloro-5-formyl-1H-pyrrole-2-carboxylic acid

HRID 1874960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874960
[Li+].[OH-].[Cl:3][C:4]1[CH:8]=[C:7]([CH:9]=[O:10])[NH:6][C:5]=1[C:11]([O:13]C)=[O:12]>C1COCC1.CO>[Cl:3][C:4]1[CH:8]=[C:7]([CH:9]=[O:10])[NH:6][C:5]=1[C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 86644900methyl 3-chloro-5-formyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 866449023-Chloro-5-formyl-1H-pyrrole-2-carboxylic acidAusbeute 114,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LiOH (2 mL, 2 mmol) was added to a solution of methyl 3-chloro-5-formyl-1H-pyrrole-2-carboxylate (0.050 g, 0.26 mmol) in THF (2 mL) and methanol (2 mL). The solution was stirred at room temperature overnight. The solvents were evaporated and the residue was partitioned between EtOAc and 1 N HCl. The organic layer was separated, dried over MgSO4, filtered and evaporated to a solid to afford the title compound (0.0517 g) as a crude product which was used with no further purification. 1H NMR (400 MHz, Acetone-d6) δ ppm 11.87 (br. s., 1H), 9.72 (s, 1H), 7.02 (s, 1H). LCMS: m/z 174.2 (M+1).

Aufarbeitung

  1. customThe solvents were evaporated
  2. customthe residue was partitioned between EtOAc and 1 N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to a solid

Quellen und Nachweise

ORD-Eintrag
ord-c732c015b5f04cb097f7069fee362c85
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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