4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamonitrile → HCID 10969638, compound

HRID 233279

Reaction equation

HRID 233279 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([CH:20]=[CH:21][C:22]#[N:23])=[CH:18][CH:17]=1>[C].[Pd].C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([CH2:20][CH2:21][C:22]#[N:23])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 536629724-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamonitrile

Product 1

HCID 10969638HCID 10969638, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamonitrile (4.0 g), palladium-carbon (5%, 0.5 g ) and ethyl acetate (50 ml) was subjected to catalytic hydrogenation at room temperature under 1 atmospheric pressure. The catalyst was filtered off, then the filtrate was concentrated under reduced pressure to leave 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionitrile (3.7 g, 93%). The product was recrystallized from ethyl acetate--hexane to give colorless needles, m.p.109°-110° C.

Workup

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

Sources & evidence

ORD record
ord-d92f7a99722f4a6f8438f5708bd80589
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Linked notes

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