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

HRID 475526
Notes
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Reaction equation

HRID 475526 reaction equation
CC(=NO)C(C)=NO.[BH4-].[Na+].[CH:11]1([CH2:17][CH2:18][O:19][C:20]2[CH:33]=[CH:32][C:23]([CH:24]=[C:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(O)(=O)C>O.[OH-].[Na+].C1COCC1.CN(C=O)C>[CH:11]1([CH2:17][CH2:18][O:19][C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 85120829HCID 85120829, compoundHCID 135459645Dimethylglyoxime

Product 1

HCID 129442145-(4-(2-Cyclohexylethoxy)benzyl)thiazolidine-2,4-dione

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

To the suspension containing CoCl2.6H2O (4.5 mg, 0.016 mmol) and dimethylglyoxime (70.1 mg, 0.6 mmol) in 10 ml of water, 4 drops of 1.0N NaOH and NaBH4 (384.6 mg, 10 mmol) were subsequently added. The mixture was cooled to 0° C., and 5-(4-(2-cyclohexylethoxy)benzylidene)thiazolidine-2,4-dione (1 g, 3.02 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-(2-cyclohexylethoxy)benzyl)thiazolidine-2,4-dione (Derivative 113 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-08f01c946a8d4c56aba40459b530e434
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637558B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes