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Lithium Hydroxide → 3-cyclopropyl-1H-pyrrole-2-carboxylic acid

HRID 524969
Notes
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Reaction equation

HRID 524969 reaction equation
[CH:1]1([C:4]2[CH:8]=[CH:7][N:6](S(C3C=CC=CC=3)(=O)=O)[C:5]=2[C:18]([O:20]C)=[O:19])[CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.O>[CH:1]1([C:4]2[CH:8]=[CH:7][NH:6][C:5]=2[C:18]([OH:20])=[O:19])[CH2:2][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 70922347HCID 70922347, compound

Product 1

HCID 793254553-cyclopropyl-1H-pyrrole-2-carboxylic acidYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of the starting methyl 3-cyclopropyl-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate (0.9 g, 3 mmol) in tetrahydrofurane (4.6 mL) and water (2.3 mL) was added lithium hydroxide (0.29 g, 12 mmol) and this mixture was heated to 100° C. in a microwave vial during 4 hours. Next, the reaction mixture was poured into water (50 mL) and this aqueous phase was washed with diethyl ether (2×). Afterwards, the aqueous layer was acidified until pH=3 by adding solid phosphoric acid and extracted with ethyl acetate (3×). The organic solution was washed with water and brine, dried (Na2SO4) and concentrated in vacuum to give 370 mg of the title compound.

Workup

  1. washthis aqueous phase was washed with diethyl ether (2×)
  2. additionby adding solid phosphoric acid
  3. extractionextracted with ethyl acetate (3×)
  4. washThe organic solution was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-b29118530622441c803f73d15e999b80
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09340547B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes