5-[3-[3-methoxy-4-[2-[(E)-styryl]-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione → 5-[3-[3-Methoxy-4-[2-(2-phenylethyl)-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione

HRID 1584316

Reaction equation

HRID 1584316 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:24][CH2:25][CH2:26][CH:27]2[O: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>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:24][CH2:25][CH2:26][CH:27]2[O: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

3

Reactant 1

HCID 698307745-[3-[3-methoxy-4-[2-[(E)-styryl]-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione

Product 1

HCID 698316175-[3-[3-Methoxy-4-[2-(2-phenylethyl)-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedioneYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[3-[3-methoxy-4-[2-[(E)-styryl]-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione (0.64 g), paradium-carbon (5%, 1.3 g) and tetrahydrofuran (THF) (35 ml) was subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to yield 5-[3-[3-methoxy-4-[2-(2-phenylethyl)-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione (0.43 g, 67%). The product was recrystallized from ethyl acetate-hexane to give colorless needles, m.p.122-123° C.

Workup

  1. customwas subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d1a33e3db30648a8a146a835c708cb6c
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Linked notes

Loading…