Acetone → HCID 9911974, compound

HRID 1885233Notes

Reaction equation

HRID 1885233 reaction equation
Cl.[OH:2][C:3]1[C:4]([CH3:32])=[C:5]2[C:10](=[C:11]([CH3:14])[C:12]=1[CH3:13])[O:9][C:8]([CH2:16][O:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][CH:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:20][CH:19]=1)([CH3:15])[CH2:7][CH2:6]2.CC(C)=[O:35]>O>[OH:35][C:8]([CH3:15])([CH2:7][CH2:6][C:5]1[C:10](=[O:9])[C:11]([CH3:14])=[C:12]([CH3:13])[C:3](=[O:2])[C:4]=1[CH3:32])[CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[NH:25][C:24]2=[O:29])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 5591Troglitazone

Product 1

HCID 9911974HCID 9911974, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 ml of an aqueous solution of ferric chloride acidified with hydrochloric acid [a mixture of about 65% by weight of ferric chloride (FeCl3.6H2O) and about 35% by weight of concentrated hydrochloric acid] were added dropwise, whilst ice-cooling and stirring, to a solution of 6.3 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidine dissolved in 50 ml of acetone, and the resulting mixture was allowed to stand overnight at room temperature. At the end of this time, the reaction mixture was diluted with 500 ml of water and then extracted with ethyl acetate. The extracts were combined, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was then removed by distillation under reduced pressure. The resulting residue was then purified by column chromatography through silica gel, using a 5:1 by volume mixture of benzene and ethyl acetate as the eluent, to afford 4.2 g of the title compound as a yellow powder softening at 55°-65° C.

Workup

  1. additionwere added dropwise, whilst ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was then removed by distillation under reduced pressure
  7. customThe resulting residue was then purified by column chromatography through silica gel
  8. additionby volume mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-7e3f6d4197a04fcbb14fe2a0f98de26b
Source dataset
uspto-grants-1992_09
Patent number
US05143930

Reaction notes

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