Acetone → 3-(4-chlorophenoxy)-2-methyl-5-(methylsulfonyl)-1H-indole-1-acetic acid, methyl ester

HRID 2233749

Reaction equation

HRID 2233749 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13](SC)[CH:14]=3)[N:9]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:8]=2[CH3:23])=[CH:4][CH:3]=1.[Na].O[O:28][S:29]([O-:31])=O.[K+].[CH3:33]C(C)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([S:29]([CH3:33])(=[O:31])=[O:28])[CH:14]=3)[N:9]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:8]=2[CH3:23])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 5360545SodiumHCID 23707502Potassium hydroxy sulfiteHCID 866092333-(4-chlorophenoxy)-2-methyl-5-(methylthio)-1H-indole-1-acetic acid, methyl ester

Product 1

HCID 866092343-(4-chlorophenoxy)-2-methyl-5-(methylsulfonyl)-1H-indole-1-acetic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product from step (ii) (0.32 g) in acetone (4 ml) and water (4 ml) was added solid sodium bicarbionate (0.57 g) followed by oxone (0.69 g in water (2.5 ml)) and the reaction was stirred for 3 h. The reaction was quenched with sodium bisulfite and partitioned between ethylacetate/water. The organics were dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 30-60% ethylacetate/iso-hexane.

Workup

  1. customThe reaction was quenched with sodium bisulfite
  2. custompartitioned between ethylacetate/water
  3. customThe organics were dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 30-60% ethylacetate/iso-hexane

Sources & evidence

ORD record
ord-25c48a8c9dae42f5a2b6048ee26a90da
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Linked notes

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