Sodium Hydroxide → HCID 86711841, compound

HRID 623757Notes

Reaction equation

HRID 623757 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([O:16]CC)=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14462625HCID 14462625, compound

Product 1

HCID 86711841HCID 86711841, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate [for synthesis see ACI-02] (2.0 g, 7.58 mmol) in dry THF (26 mL) and MeOH (26 mL) was added aqueous 6 M NaOH (25.3 mL, 152 mol) and the mixture was stirred at reflux for 3 h. The organic solvents were evaporated and the remainder was acidified with aqueous 6 M HCl (30 mL) at 0° C. The resulting mixture was extracted with EtOAc (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated to yield the desired product 1.71 g, 96%).

Workup

  1. temperatureat reflux for 3 h
  2. customThe organic solvents were evaporated
  3. customwas acidified with aqueous 6 M HCl (30 mL) at 0° C
  4. extractionThe resulting mixture was extracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e1004d1468e4934914b3adcbdeca9bc
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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