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

HRID 233285

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-aa643455dbce476a92fbbdb8646e5997
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05591862

Linked notes

Loading…