Sodium Hydroxide → HCID 59852985, compound

HRID 2374054Notes

Reaction equation

HRID 2374054 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][S:7]([CH2:9][C:10]([O:12]CC)=[O:11])=[O:8])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][S:7]([CH2:9][C:10]([OH:12])=[O:11])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59853076HCID 59853076, compound

Product 1

HCID 59852985HCID 59852985, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-fluorobenzylsulfinyl)acetate (1.60 g, 6.55 mmol) in THF (10.0 mL) and MeOH (20.0 mL) was added 1 N NaOH (20.0 mmol). The mixture was stirred at room temperature for 2 h. After removal of organic solvent under reduced pressure, the remaining aqueous solution was neutralized with 1 N HCl (25.0 mL). It was extracted with EtOAc (3×100 mL) and the combined organic layer was dried over MgSO4. The solution was then filtered and concentrated in vacuo to give 2-(4-fluorobenzylsulfinyl)acetic acid (1.25 g, 88% yield). MS(ESI+): m/z 217.05 (M+H)+.

Workup

  1. customAfter removal of organic solvent under reduced pressure
  2. extractionIt was extracted with EtOAc (3×100 mL)
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. filtrationThe solution was then filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cae787bae816455bbbc9d072ed768e33
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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