Sodium Hydroxide → HCID 66670176, compound

HRID 1514639Notes

Reaction equation

HRID 1514639 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([O:22]CC)=[O:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O1CCCC1>[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:8]([CH3:19])=[C:7]([C:20]([OH:22])=[O:21])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66670203HCID 66670203, compound

Product 1

HCID 66670176HCID 66670176, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 15.91 g portion of ethyl 5-tert-butyl-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate was dissolved in a mixture of 200 ml of ethanol and 20 ml of tetrahydrofuran at 80° C., and 96.01 ml of a 5 M sodium hydroxide aqueous solution was added thereto, followed by overnight stirring at the same temperature and then further stirring at 100° C. for 6 hours. The reaction liquid was concentrated to about 150 ml, and, under ice-cooling, 6 M hydrochloric acid was added thereto until pH became 1. The resulting solid was collected by filtration and washed with water to obtain 14.04 g of 5-tert-butyl-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylic acid as a light brown solid.

Workup

  1. stirringfurther stirring at 100° C. for 6 hours
  2. customThe reaction liquid
  3. concentrationwas concentrated to about 150 ml
  4. temperatureunder ice-cooling
  5. addition6 M hydrochloric acid was added
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-d77c35020c714614af3438305059726e
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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