Acetone → HCID 53670423, compound

HRID 1955716Notes

Reaction equation

HRID 1955716 reaction equation
I([O-])(=O)(=O)=O.[Na+].[F:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH2:27][C:28]([OH:30])=[O:29])=[C:13]([CH3:26])[C:14]2=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[CH:10][C:9]=1[O:31][CH3:32].CC(C)=[O:35]>O.CO>[F:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH2:27][C:28]([OH:30])=[O:29])=[C:13]([CH3:26])[C:14]2=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:25])=[O:35])=[CH:20][CH:19]=2)=[CH:10][C:9]=1[O:31][CH3:32]

Participants

6

Reactant 3

HCID 180AcetoneHCID 23667635Sodium periodateHCID 54501266HCID 54501266, compound

Product 1

HCID 53670423HCID 53670423, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium periodate, 4.28 g (20 mol) in 40 ml of water is added dropwise to 6-fluoro-5-methoxy-2-methyl-1-(p-methylthiobenzylidene)-3-indenylacetic acid, 3.70 g (10 mmol) in 300 ml methanol and enough acetone to cause solution. This solution is stirred overnight at room temperature and filtered. The filtrate is evaporated at 30° to a small volume which causes the product to precipitate. The suspension is diluted with several volumes of water, and is cooled. Collected crystals are washed with water and methanol-water (1:1). The product is dried in vacuo over potassium hydroxide pellets and then in a vacuum oven at 70° C. The crude product is recrystallized from methylene chloride-petroleum ether to give 6-fluoro-5-methoxy-2-methyl-1-(p-methylsulfinyl-benzylidene)-3-indenylacetic acid (m.p. 190°-193°). 6-fluoro-5-methoxy -2-methyl-1-(p-methylsulfonylbenzylidene)-3-indenylacetic acid is prepared according to the procedure of Example 1, part G by the addition of 1.0 mol of m-chloroperbenzoic acid per mol of 6-fluoro-5-methoxy-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl acetic acid in an acetone solution.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated at 30° to a small volume which
  3. customto precipitate
  4. additionThe suspension is diluted with several volumes of water
  5. temperatureis cooled
  6. customCollected crystals
  7. washare washed with water and methanol-water (1:1)
  8. dry with materialThe product is dried in vacuo over potassium hydroxide pellets
  9. customat 70° C
  10. customThe crude product is recrystallized from methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-693793c101fb41eba41f2137d8fa5002
Source dataset
uspto-grants-1998_07
Patent number
US05776962

Reaction notes

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