5-[(2-(3-Phenylpropionyl)-5-pyridyl)methylene]thiazolidine-2,4-dione → 5-[(2-(3-Phenyl-1-hydroxypropyl)-5-pyridyl)methyl]thiazolidine-2,4-dione

HRID 346200

Reaction equation

HRID 346200 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[C:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:13][N:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Na].[Hg]>[C:1]1([CH2:7][CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:13][N:12]=2)[OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 543159385-[(2-(3-Phenylpropionyl)-5-pyridyl)methylene]thiazolidine-2,4-dione

Product 1

HCID 144599355-[(2-(3-Phenyl-1-hydroxypropyl)-5-pyridyl)methyl]thiazolidine-2,4-dioneYield 36%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 887MethanolSolvent

Procedure

To a solution of the title product of Example 67 (260 mg, 0.77 mmol) in methanol (10 ml) was added 3% sodium amalgam (4 g) and the reaction was stirred for 4 hours. The methanol was decanted, evaporated and the resultant solid diluted with water (10 ml). The aqueous solution was adjusted to pH 2 with 1N HCl and extracted with CH2Cl2 (3×10 ml) which was discarded. After neutralization of the aqueous layer to pH 7 with NaHCO3, it was then re-extracted with CH2Cl2 (3×10 ml). These combined organic layers were dried (MgSO4), filtered and concentrated to afford the desired product (94 mg, 36%) isolated as a foam.

Workup

  1. customThe methanol was decanted
  2. customevaporated
  3. additionthe resultant solid diluted with water (10 ml)
  4. extractionextracted with CH2Cl2 (3×10 ml) which
  5. extractionAfter neutralization of the aqueous layer to pH 7 with NaHCO3, it was then re-extracted with CH2Cl2 (3×10 ml)
  6. dry with materialThese combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c5553ede90a74f53abf52e55e90825be
Source dataset
uspto-grants-1991_10
Patent number
US05061717

Linked notes

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