Methanol → HCID 54032229, compound

HRID 263623Notes

Reaction equation

HRID 263623 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1)[C:6]([CH3:21])=[C:5]2[CH2:22][C:23]([OH:25])=[O:24].CO.I([O-])(=O)(=O)=[O:29].[Na+].O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:20])=[O:29])=[CH:15][CH:14]=1)[C:6]([CH3:21])=[C:5]2[CH2:22][C:23]([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962Water2×HCID 23667635Sodium periodateHCID 54220384HCID 54220384, compound

Product 1

HCID 54032229HCID 54032229, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 0.358 g. (1.0 mole) of 5,6-difluoro-2-methyl-1-(ρ-methylthiobenzylidene)-indene-3-acetic acid in acetone (10 ml.) is added 10-15 ml. MeOH. With magnetic stirring, 0.32 g. (1.5 mole) of sodium meta periodate is added in 5 ml. of water. The proportions of acetone, methanol and water are adjusted if necessary to preserve homogeneity. After several minutes, a precipitation of sodium iodate appears. The suspension is stirred at room temperature for 16 hours, and then poured into approximately 50 ml. of water and 100 ml. methylene chloride. The two phases are separated and the water layer is extracted twice with methylene chloride. The organic phases are washed with water and dried (MgSO4). The residue after evaporation is dissolved in the minimum amount of boiling ethyl acetate and allowed to stand for 12 hours in the freezer compartment. The deep orange crystals are filtered. The filtrate is reduced to 1/2 volume and allowed to stand in the cold for several hours to give a large second crop. In this way, 5,6-difluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenylacetic acid is isolated, M.P. 200°-210°, which is converted to 5,6-difluoro-2-methyl-1-(p-methylsulfonylbensylidene)-3-indenylacetic acid with the procedure of Example 1. (R1 =hydrogen; R2 =CH3 ; R3 =5-fluoro; R4 =6-fluoro; R5 =CH3 --SO2).

Workup

  1. waitAfter several minutes
  2. customa precipitation of sodium iodate
  3. additionpoured into approximately 50 ml
  4. customThe two phases are separated
  5. extractionthe water layer is extracted twice with methylene chloride
  6. washThe organic phases are washed with water
  7. dry with materialdried (MgSO4)
  8. customThe residue after evaporation
  9. dissolutionis dissolved in the minimum amount of boiling ethyl acetate
  10. waitto stand for 12 hours in the freezer compartment
  11. filtrationThe deep orange crystals are filtered
  12. customcold for several hours
  13. customto give a large second crop

Sources & evidence

ORD record
ord-3c146c821cb6483b910a99ede18a1953
Source dataset
uspto-grants-1997_07
Patent number
US05643959

Reaction notes

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