Sodium Hydroxide → HCID 54537837, compound

HRID 2228004Notes

Reaction equation

HRID 2228004 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54159384HCID 54159384, compound

Product 1

HCID 54537837HCID 54537837, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product from step B (E and Z isomers) (2.3 g, 6.8 mmol) in methanol (50 ml) was treated with 2N aqueous sodium hydroxide solution (7 ml, 14 mmol) for 1 hour. Methanol was then evaporated and the solution was acidified to pH 5.5 with 6N HCl. The resulting precipitate was triturated in ether and filtered to give 4-(-2-(4-fluorophenyl)-3-(imidazol-1-yl)-prop-1-en-1-yl)benzoic acid as a mixture of E and Z isomers 1.4 g (65%).

Workup

  1. customMethanol was then evaporated
  2. customThe resulting precipitate was triturated in ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d9b37df993934a37a11dffcb33e104cb
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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