Dimethylformamide → (E)-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]acrylonitrile

HRID 233285

Reaktionsgleichung

Br[CH:2]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[N:10][CH:11]=1)[C:3]#[N:4].[Br-].[Li+].C(=O)([O-])[O-].[Li+].[Li+].CN(C)C=O>O>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:16][C:15]=1[CH2:14][CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6](/[CH:5]=[CH:2]/[C:3]#[N:4])=[CH:11][N:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 2-bromo-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]propionitrile (4.5 g), lithium bromide (LiBr) (1.14 g), lithium carbonate (Li2CO3) (2.17 g) and N,N-dimethylformamide (50 ml) was stirred for 2.5 hours at 120° C. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure to leave (E)-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]acrylonitrile (3.2, 89%), which was recrystallized from ethyl acetate--hexane to give pale yellow crystals, m.p.116°-117° C.

Aufarbeitung

extractionwas subjected to extraction with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried (MgSO4)
distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-aa643455dbce476a92fbbdb8646e5997
Quelldatensatz: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05591862

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