Methanol → HCID 53670423, compound

HRID 263630Notes

Reaction equation

HRID 263630 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH2:7].[F:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH2:28][C:29]([OH:31])=[O:30])=[C:14]([CH3:27])[C:15]2=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=2)=[CH:11][C:10]=1[O:32][CH3:33].CO>CC(C)=O>[F:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH2:28][C:29]([OH:31])=[O:30])=[C:14]([CH3:27])[C:15]2=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:26])=[O:7])=[CH:21][CH:20]=2)=[CH:11][C:10]=1[O:32][CH3:33]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23667635Sodium periodateHCID 54501266HCID 54501266, compound

Product 1

HCID 53670423HCID 53670423, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of sodium periodate, 4.28 g. (20 mole) in 40 ml. of water is added dropwise to 6-fluoro-5-methoxy-2-methyl-1-(ρ-methylthiobenzylidene)-3-indenyl acetic acid, 3.70 g. (10 mole) in 300 ml. methanol and enough acetone to cause solution. This solution is stirred over night 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, cooled and collected. After rinsing with water and cold 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-(ρ-methylsulfinylbenzylidene)-3-indenyl acetic acid (M.P. 190°-193°).

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. temperaturecooled
  6. customcollected
  7. washAfter rinsing with water and cold 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-f898a0ae6c2447b7aedecf376328b039
Source dataset
uspto-grants-1997_07
Patent number
US05643959

Reaction notes

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