5-(4-Isopropoxy-3-methoxycinnamylidene)-2,4-oxazolidinedione → 5-[3-(4-Isopropoxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedione

HRID 1584297Notes

Reaction equation

HRID 1584297 reaction equation
[CH:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([CH:9]=[CH:10][CH:11]=[C:12]2[O:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:7][C:6]=1[O:21][CH3:22])([CH3:3])[CH3:2]>[C].[Pd].O1CCCC1>[CH:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][CH2:10][CH2:11][CH:12]2[O:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:7][C:6]=1[O:21][CH3:22])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 570005285-(4-Isopropoxy-3-methoxycinnamylidene)-2,4-oxazolidinedione

Product 1

HCID 698306285-[3-(4-Isopropoxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedioneYield 60%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-isopropoxy-3-methoxycinnamylidene)-2,4-oxazolidinedione (7.1 g), palladium-carbon (5%, 7.1 g) and tetrahydrofuran (THF) (150 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. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-ethyl acetate (4:1), 5-[3-(4-isopropoxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedione (4.3 g, 60%) was obtained as an oily product.

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
  4. washFrom the fraction eluted with chloroform-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-a1bf26b4a7034f5cac78671fbd5fd60c
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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