Thiazolidinedione → 5-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl)-propyl}-2-methyl-benzylidene)-thiazolidine-2,4-dione

HRID 230825Notes

Reaction equation

HRID 230825 reaction equation
[CH2:1]([C:3]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([CH3:29])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[S:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:1]([C:3]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[C:34]2[S:30][C:31](=[O:36])[NH:32][C:33]2=[O:35])=[C:23]([CH3:29])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:18])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 9793820Piperidine, acetateHCID 577634244-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde

Product 1

HCID 866047825-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl)-propyl}-2-methyl-benzylidene)-thiazolidine-2,4-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of enantiomer 1 of 4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde (0.64 g, 1.61 mmol) and toluene (20 mL) is added 90% 2,4-thiazolidinedione (0.25 g, 1.94 mmol), and piperidine acetate (0.04 g, 0.24 mmol). The solution is heated to a reflux overnight and the water removed by a Dean-Stark trap. The solution is diluted with EtOAc (60 mL), washed with water (50 mL), saturated NaHCO3 (50 mL), dried over MgSO4, filtered and concentrated. Purified by ISCO (20%-50% EtOAc gradient) to furnish the title compound (0.75 g, 1.51 mmol, 94%).

Workup

  1. temperatureThe solution is heated to a reflux overnight
  2. customthe water removed by a Dean-Stark trap
  3. additionThe solution is diluted with EtOAc (60 mL)
  4. washwashed with water (50 mL), saturated NaHCO3 (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurified by ISCO (20%-50% EtOAc gradient)

Sources & evidence

ORD record
ord-905f5f9754a44b70aa88356ee5bf5bf6
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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