Lithium Hydroxide → HCID 57423711, compound

HRID 1725174Notes

Reaction equation

HRID 1725174 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:7]=[C:6]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Li+].[OH-]>C1COCC1>[CH2:16]([C:6]1[N:5]([CH2:4][C:3]([OH:23])=[O:2])[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57423710HCID 57423710, compound

Product 1

HCID 57423711HCID 57423711, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl(2-benzyl-5-phenyl-1H-pyrrol-1-yl)acetate (203 mg, 0.66 mmol) in THF (1 ml) was added aqueous 1N LiOH (1 ml) at room temperature. After 3 h stirring at room temperature, the reaction was quenched with H2O (10 ml). The aqueous was extracted with Et2O (2×10 ml). The aqueous was acidified with 1N HCl to pH˜3, extracted with EtOAc (3×15 ml). The combined organic extracts were washed with H2O (15 ml), brine (15 ml), dried (Na2SO4) and concentrated. The crude material was purified by chromatography (EtOAc/MeOH: 95/5) to provid the titled compound (185 mg, 96%) as a solid: mp 137-139° C.; MS (+) ES, 292 (M+H)+.

Workup

  1. customthe reaction was quenched with H2O (10 ml)
  2. extractionThe aqueous was extracted with Et2O (2×10 ml)
  3. extractionextracted with EtOAc (3×15 ml)
  4. washThe combined organic extracts were washed with H2O (15 ml), brine (15 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by chromatography (EtOAc/MeOH: 95/5)

Sources & evidence

ORD record
ord-fc77a540f72248e6a58b397c9a3efecc
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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