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Hydrochloric Acid → 2-[2-Methyl-4-(trifluoromethyl)-5-vinylimidazol-1-yl]pent-4-enoic acid

HRID 1754373
Notes
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Reaction equation

HRID 1754373 reaction equation
[CH3:1][C:2]1[N:3]([CH:13]([CH2:19][CH:20]=[CH2:21])[C:14]([O:16]CC)=[O:15])[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[OH-].[Na+].Cl>CCO>[CH3:1][C:2]1[N:3]([CH:13]([CH2:19][CH:20]=[CH2:21])[C:14]([OH:16])=[O:15])[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86724377Ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enoate

Product 1

HCID 867243782-[2-Methyl-4-(trifluoromethyl)-5-vinylimidazol-1-yl]pent-4-enoic acidYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enoate (127 mg, 0.42 mmol) was added EtOH (2 mL) and 5 N NaOH (0.5 mL), and the resulting solution was stirred at room temperature for 1 h. 12 N HCl was added slowly at room temperature until the solution reached pH 2, followed by concentration in vacuo to obtain 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enoic acid (100 mg, crude) which was used as such in the next step without further purification.

Workup

  1. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-d1c3ff210e9e4796bf053b825354e982
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09169248B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes