Hydrochloric Acid → HCID 22261931, compound

HRID 1610669Notes

Reaction equation

HRID 1610669 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:29])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])[CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:29])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593290HCID 86593290, compound

Product 1

HCID 22261931HCID 22261931, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(4-bromophenyl)-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (19.5 g, 40.7 mmol) in methanol (100 ml) was added 2N aqueous sodium hydroxide solution (40.7 ml, 81.4 mmol) and the mixture was stirred at room temperature for 2.5 hrs. 6N Hydrochloric acid (50 ml) was added to acidify the solution and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from hexane to give the objective substance (16.7 g, 91%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from hexane
  6. customto give the objective substance (16.7 g, 91%)

Sources & evidence

ORD record
ord-055eda60313e4bcc9354aef6ea54f853
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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