HCID 86754594, compound → HCID 86754593, compound

HRID 1739026Notes

Reaction equation

HRID 1739026 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:24][CH2:25][CH2:26][CH:27]2[S:31][C:30](=[O:32])[NH:29][C:28]2=[O:33])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:14][CH:15]=1>[C].[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:24][CH2:25][CH2:26][CH:27]2[S:31][C:30](=[O:32])[NH:29][C:28]2=[O:33])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:14][CH:15]=1

Participants

4

Reactant 1

HCID 86754594HCID 86754594, compound

Product 1

HCID 86754593HCID 86754593, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[3-[3-methoxy-4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2,4-thiazolidinedione (0.37 g), palladium-carbon (5%, 0.74 g) and tetrahydrofuran (20 ml) was subjected to catalytic hydrogenation at 1 atm and room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give crystals. The crystals were recrystallized from ethyl acetate-hexane to give 5-[3-[3-methoxy-4-(2-phenethyl-4-oxazolylmethoxy)phenyl]propyl]-2,4-thiazolidinedione (0.20 g, 54%). Colorless prisms, mp: 126-127° C.

Workup

  1. customwas subjected to catalytic hydrogenation at 1 atm and room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give crystals
  5. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-aca71a5c6fbd40009effa4ede0e316e4
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

Loading…