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

HRID 233285

반응식

HRID 233285 반응식
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

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11125Lithium CarbonateHCID 82050Lithium BromideHCID 109385272-Bromo-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]propionitrile

생성물 1

HCID 23361351(E)-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]acrylonitrile수율 89%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-aa643455dbce476a92fbbdb8646e5997
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591862

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