Lithium Hydroxide → HCID 70816435, compound

HRID 1843017Notes

Reaction equation

HRID 1843017 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:19])[C:14]([O:16]CC)=[O:15])[CH:5]=[CH:6][C:7]=1[CH2:8][S:9]([CH3:12])(=[O:11])=[O:10].O1CCCC1.[OH-].[Li+]>O.C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:19])[C:14]([OH:16])=[O:15])[CH:5]=[CH:6][C:7]=1[CH2:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 70815867HCID 70815867, compound

Product 1

HCID 70816435HCID 70816435, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of ethyl 2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)propanoate (950 mg, 3.295 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added lithium hydroxide (236 mg, 9.885 mmol). The reaction mixture was refluxed for overnight, then cooled to room temperature, diluted with water (25 mL) and diethyl ether (25 mL). After phase separation the aqueous layer was acidified by HCl to a pH=3 and extracted with DCM (3×50 mL). The organic layer was dried over magnesium sulfate and filtered. The solvent of the filtrate was removed in vacuo to give 2-(3-fluoro-4-(methylsulfonylmethyl)-phenyl)propanoic acid (846 mg, 99%).

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. customAfter phase separation the aqueous layer
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent of the filtrate was removed in vacuo

Sources & evidence

ORD record
ord-d22bbdd25017468e922f39c2fd5aac51
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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