Ethanol → 5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid

HRID 263636Notes

Reaction equation

HRID 263636 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:20])=[O:19])=[CH:14][CH:13]=1)[C:6]([CH3:21])=[C:5]2[CH2:22]C(NCC(O)=O)=O.[CH2:30]([OH:32])C.[OH-:33].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[CH:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([CH3:20])=[O:19])=[CH:16][CH:17]=1)[C:6]([CH3:21])=[C:5]2[CH2:22][C:30]([OH:32])=[O:33]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70150105HCID 70150105, compound

Product 1

HCID 53525-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[5-fluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenylacetyl]-glycine. Benzyle-N-[5-fluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenylacetyl]-glycinate (0.03 mole) in a mixture of 25 ml. of anhydrous ethanol and 2.5 ml. of 1N sodium hydroxide is allowed to stand at room temperature for 18 hours. The solution is diluted with water and extracted with ether. The aqueous layer is acidified with dilute hydrochloric acid and the organic product is extracted with ethyl acetate, washed with water and dried over sodium sulfate. Evaporation of the solution gives N-[5-fluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenylacetic acid, the corresponding indenyl acyl glycine is obtained, which can be converted to the corresponding sulfonyl derivative using the procedure of Example 1E.

Workup

  1. extractionextracted with ether
  2. extractionthe organic product is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solution

Sources & evidence

ORD record
ord-9f9891949e254cae9262f5b80d86bcca
Source dataset
uspto-grants-1997_07
Patent number
US05643959

Reaction notes

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