Benzene → 5-[4-(6-Hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-yl-methoxy)benzyl]thiazolidine-2,4-dione

HRID 1030372Notes

Reaction equation

HRID 1030372 reaction equation
O[CH:2]1[C:11]2[C:6](=[C:7]([CH3:15])[C:8]([CH3:14])=[C:9]([OH:13])[C:10]=2[CH3:12])[O:5][C:4]([CH2:17][O:18][C:19]2[CH:32]=[CH:31][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:20]=2)([CH3:16])[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>CN(C)C=O>[OH:13][C:9]1[C:10]([CH3:12])=[C:11]2[C:6](=[C:7]([CH3:15])[C:8]=1[CH3:14])[O:5][C:4]([CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:20]=1)([CH3:16])[CH:3]=[CH:2]2

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 136058355-[4-(4,6-Dihydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 150938375-[4-(6-Hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-yl-methoxy)benzyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 140 mg of 5-[4-(4,6-dihydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Example 30), 10 mg of p-toluenesulfonic acid, 10 ml of benzene and 0.5 ml of dimethylformamide was heated under reflux for 1 hour. The reaction solution was cooled, washed with a saturated aqueous solution of sodium bicarbonate and then with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography eluted with a 4:1 by volume mixture of benzene and ethyl acetate, to give the title compound, softening at 173°-176° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction solution was cooled
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialwith water and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-af3dcb2bd82641cbb3fecccbf0e221e1
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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