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 230829Notes

Reaction equation

HRID 230829 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 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of enantiomer 2 of 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde (048 g, 1.21 mmol) and toluene (15 mL) is added 90% 2,4-thiazolidinedione (0.19 g, 1.45 mmol), and piperidine acetate (0.03 g, 0.18 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), brine (50 mL), dried over MgSO4, filtered and concentrated. Purified by ISCO (20%-40% EtOAc gradient) to furnish the title compound (0.50 g, 1.00 mmol, 83%).

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), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurified by ISCO (20%-40% EtOAc gradient)

Sources & evidence

ORD record
ord-510cc1c2af4e4680811dbc67aa743265
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

Loading…