Thiazolidinedione → HCID 11211219, compound

HRID 233767Notes

Reaction equation

HRID 233767 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].CN(C)P(=O)(N(C)C)N(C)C.[CH2:19]([Li])CCC.[F:24][C:25]1[CH:44]=[CH:43][CH:42]=[CH:41][C:26]=1[CH2:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[C:34](CI)[CH:33]=[CH:32]2>C1COCC1.CCCCCC.C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>[F:24][C:25]1[CH:44]=[CH:43][CH:42]=[CH:41][C:26]=1[CH2:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[C:34]([CH:5]1[S:1][C:2](=[O:7])[N:3]([CH3:19])[C:4]1=[O:6])[CH:33]=[CH:32]2

Participants

9

Reactant 4

HCID 5437ThiazolidinedioneHCID 12679HexamethylphosphoramideHCID 23356925HCID 23356925, compoundHCID 178418339Butyllithium

Product 1

HCID 11211219HCID 11211219, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 2,4-thiazolidinedione (108 mg) in THF (5 ml) was added hexamethylphosphoric triamide (0.5 ml) and the resulting mixture was cooled to -30° C., and n-butyllithium (1.6M, a solution in hexane) (1.1 ml) was added thereto. The mixture was stirred at -30° C. for 30 minutes and a solution of 6-(2-fluorobenzyloxy)-2-naphthylmethyl iodide (0.24 g) in THF (3 ml) was added. The resulting mixture was gradually warmed from -30° C. to room temperature and stirred for 6 hours. After reaction, ethyl acetate was added to the above reaction mixture. The organic layer was washed with an aqueous solution of ammonium chloride and a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a residue. The residue was subjected to column chromatography on silica gel eluting with ethyl acetate/hexane to obtain an amorphous solid. The solid was recrystallized from ethyl acetate/hexane to obtain the title compound (152 mg, yield=65%). The NMR spectrum, IR spectrum and melting point are as follows.

Workup

  1. temperatureThe resulting mixture was gradually warmed from -30° C. to room temperature
  2. stirringstirred for 6 hours
  3. additionwas added to the above reaction mixture
  4. washThe organic layer was washed with an aqueous solution of ammonium chloride
  5. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue
  8. customto obtain an amorphous solid
  9. customThe solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a7388e394a2e48bca8ddb4285dc11857
Source dataset
uspto-grants-1997_01
Patent number
US05594016

Reaction notes

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