Acetic Acid → 5-(4-(Benzyloxy)benzyl)thiazolidine-2,4-dione

HRID 475529Notes

Reaction equation

HRID 475529 reaction equation
CC(=NO)C(C)=NO.[BH4-].[Na+].[CH2:11]([O:18][C:19]1[CH:32]=[CH:31][C:22]([CH:23]=[C:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C>O.[OH-].[Na+].C1COCC1.CN(C=O)C>[CH2:11]([O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 3096180HCID 3096180, compoundHCID 4311764Sodium borohydrideHCID 135459645Dimethylglyoxime

Product 1

HCID 443192685-(4-(Benzyloxy)benzyl)thiazolidine-2,4-dione

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolvent2×HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To the suspension containing CoCl2.6H2O (4.49 mg, 0.016 mmol) and dimethylglyoxime (74.54 mg, 0.64 mmol) in 10 ml of water, 4 drops of 1.0N NaOH and NaBH4 (417.1 mg, 10.85 mmol) were subsequently added. The mixture was cooled to 0° C., and 5-(4-(benzyloxy)benzylidene)thiazolidine-2,4-dione (1 g, 3.27 mmol) in 15 ml of THF-DMF (2:1) was added thereto over 20 minutes. The mixture was stirred at room temperature for 18 hours, to which acetic acid was then added until the pH thereof reached about 6. The mixture was diluted with water and extracted with ethyl acetate and water. The organic layer was washed with water several times, dried with anhydrous magnesium sulfate, filtered and solvent-evaporated. The residual oil was chromatographed on silica gel to afford 5-(4-(benzyloxy)benzyl)thiazolidine-2,4-dione (Derivative 116 of the above formula) as white solid (0.8 g, yield: 79%).

Workup

  1. additionwere subsequently added
  2. additionwas then added until the pH
  3. extractionextracted with ethyl acetate and water
  4. washThe organic layer was washed with water several times
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customsolvent-evaporated
  8. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-5aa16f9af2634ca49c29a80a16c1b3b2
Source dataset
uspto-grants-2014_01
Patent number
US08637558B2

Reaction notes

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