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Water → (Z)-5,6-difluoro-2-methyl-1-(p-methylsulfonylbenzylidene)-indene-3-acetic acid

HRID 377757
Notes
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Reaction equation

HRID 377757 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[CH2:7][C:6]([CH3:12])=[C:5]2[CH2:13][C:14]([O:16]C)=[O:15].[CH3:18][S:19]([C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1)(=[O:21])=[O:20].O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])/[C:7](=[CH:26]\[C:25]1[CH:24]=[CH:23][C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:29][CH:28]=1)/[C:6]([CH3:12])=[C:5]2[CH2:13][C:14]([OH:16])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962Water2×HCID 2203764-(Methylsulfonyl)benzaldehydeHCID 12052144Methyl 5,6-difluoro-2-methylindene-3-acetate

Product 1

HCID 70288966(Z)-5,6-difluoro-2-methyl-1-(p-methylsulfonylbenzylidene)-indene-3-acetic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 5,6-difluoro-2-methylindene-3-acetate (1.19 g, 5.0 mmol) from Example 2, Part E and of p-methylsulfonylbenzaldehyde (0.76 g, 5.0 mmol) in dry pyridine (10 ml) are treated under nitrogen with Triton B (5.0 g, 5.1 mmol). The deeply colored solution is kept overnight. Water (2 ml) is added, the solution is stirred for 15 minutes and is poured into excess water. The mixture is extracted with ether (2×50 ml). The aqueous phase is added to 10% HCl-ice. The solution of the precipitate is extracted into methylene chloride and is dried (MgSO4). The solvent is evaporated to leave an orange solid which is recrystallized from benzene to give (Z)-5,6-difluoro-2-methyl-1-(p-methylsulfonylbenzylidene)-indene-3-acetic acid.

Workup

  1. extractionThe mixture is extracted with ether (2×50 ml)
  2. additionThe aqueous phase is added to 10% HCl-ice
  3. extractionThe solution of the precipitate is extracted into methylene chloride
  4. dry with materialis dried (MgSO4)
  5. customThe solvent is evaporated
  6. customto leave an orange solid which
  7. customis recrystallized from benzene

Sources & evidence

ORD record
ord-5f0ad651339a4210bcd234822b133a3f
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06028116

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes