3,5-Dimethoxyphenylacetonitrile → (2Z)-2-(3,5-dimethoxyphenyl)-3-{4-[(8-hydroxyoctyl)oxy]phenyl}prop-2-enenitrile

HRID 2204900

반응식

HRID 2204900 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH2:27][C:28]#[N:29])[CH:24]=[C:23]([O:30][CH3:31])[CH:22]=1>CC(O)C.CO>[CH3:31][O:30][C:23]1[CH:24]=[C:25](/[C:27](=[CH:15]/[C:14]2[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:12][CH:13]=2)/[C:28]#[N:29])[CH:26]=[C:21]([O:20][CH3:19])[CH:22]=1

참가 물질

5

반응물 2

HCID 1394453,5-DimethoxyphenylacetonitrileHCID 867251284-[(8-Hydroxyoctyl)oxy]benzaldehyde

생성물 1

HCID 71272595(2Z)-2-(3,5-dimethoxyphenyl)-3-{4-[(8-hydroxyoctyl)oxy]phenyl}prop-2-enenitrile수율 43.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3776Isopropanol용매

반응 조건

온도
60 °C

실험 절차

5.0 g (20.0 mmol) of 4-[(8-hydroxyoctyl)oxy]benzaldehyde, 3.5 g (19.8 mmol) of 3,5-(dimethoxyphenyl)acetonitrile are dissolved in 50 mL of propan-2-ol. The solution is heated to 60° C. and 2.0 mL (2.0 mmol) of a one molar solution of tetrabuthylamoniumhydroxyde in methanol are added drop wise. After 2 h at 60° C., the reaction mixture is cooled to 0° C. The precipitate is filtered off, washed with cold propan-2-ol and recristalized in propan-2-ol. 3.5 g of (2Z)-2-(3,5-dimethoxyphenyl)-3-{4-[(8-hydroxyoctyl)oxy]phenyl}prop-2-enenitrile are obtained as a white solid (42% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.

후처리

  1. temperaturethe reaction mixture is cooled to 0° C
  2. filtrationThe precipitate is filtered off
  3. washwashed with cold propan-2-ol

출처 및 근거

ORD 기록
ord-271e0bf14ad540459f4defeff5ed9691
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09366906B2

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