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

HRID 1874960Notes

Reaction equation

HRID 1874960 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 866449023-Chloro-5-formyl-1H-pyrrole-2-carboxylic acidYield 114.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c732c015b5f04cb097f7069fee362c85
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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