Sodium Hydroxide → HCID 22261525, compound

HRID 1610620Notes

Reaction equation

HRID 1610620 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:29]=[CH:28][C:19]3[O:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[O:23][C:18]=3[CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:29]=[CH:28][C:19]3[O:20][C:21]([F:26])([F:27])[C:22]([F:25])([F:24])[O:23][C:18]=3[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593280HCID 86593280, compound

Product 1

HCID 22261525HCID 22261525, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methyl]propanoate (4.20 g, 9.71 mmol) in methanol (20 ml) was added 2N aqueous sodium hydroxide solution (9.7 ml, 19.4 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated, acidified with 1N hydrochloric acid and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the objective substance (3.50 g, 89%)

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with ethyl acetate (200 ml×2)
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-hexane
  7. customto give the objective substance (3.50 g, 89%)

Sources & evidence

ORD record
ord-edf0bb2d4c8047d4bdd4f23a6ba10929
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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