Sodium Hydroxide → HCID 19365933, compound

HRID 850104Notes

Reaction equation

HRID 850104 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH2:27])[C:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])([OH:18])[CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:11]([OH:18])([C:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=1)=[CH2:27])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54102178HCID 54102178, compound

Product 1

HCID 19365933HCID 19365933, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(2-[2,4-difluorophenyl]-2-hydroxy-1-(1,2,4-triazol-1-yl)-3-buten-3-yl) benzoic acid methyl ester (see Preparation 23 part (i)) (3.44 g, 9 mmol) in a mixture of methanol (50 ml) and aqueous sodium hydroxide (2M, 9 ml, 18 mmol) was heated under reflux for 3 hours. The cooled solution was evaporated under reduced pressure and the residue was dissolved in water (30 ml). The aqueous solution was extracted with ethyl acetate (3×30 ml) before acidification with hydrochloric acid (2M). The aqueous phase was further extracted with ethyl acetate (3×30 ml). The combined organic extracts were washed with brine (3×20 ml), dried (Na2SO4) and evaporated under reduced pressure to yield 4-{2-[2,4-difluorophenyl]-2-hydroxy-1-(1,2,4-triazol-1-yl)-3-buten-3-yl} benzoic acid (3.2 g, 96%). Recrystallisation of a sample from ethyl acetate/hexane/methanol afforded an off-white solid, m.p. 189-190° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe cooled solution was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water (30 ml)
  5. extractionThe aqueous solution was extracted with ethyl acetate (3×30 ml) before acidification with hydrochloric acid (2M)
  6. extractionThe aqueous phase was further extracted with ethyl acetate (3×30 ml)
  7. washThe combined organic extracts were washed with brine (3×20 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-03716e97a9c944d7ae7c909f6a3e52ff
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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