Diisopropylamine → 4-[1,1-Dimethyl-2-oxo-3-(2-pyrazinyl)propoxy]benzonitrile

HRID 1073957노트

반응식

HRID 1073957 반응식
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1.[C:20]([C:22]1[CH:36]=[CH:35][C:25]([O:26][C:27]([CH3:34])([CH3:33])[C:28](OCC)=[O:29])=[CH:24][CH:23]=1)#[N:21]>CCCCCC.O1CCCC1.O>[CH3:33][C:27]([CH3:34])([O:26][C:25]1[CH:35]=[CH:36][C:22]([C:20]#[N:21])=[CH:23][CH:24]=1)[C:28](=[O:29])[CH2:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1

참가 물질

8

반응물 4

HCID 7912DiisopropylamineHCID 79762-MethylpyrazineHCID 205808Propanoic acid, 2-(4-cyanophenoxy)-2-methyl-, ethyl esterHCID 178418339Butyllithium

생성물 1

HCID 198956054-[1,1-Dimethyl-2-oxo-3-(2-pyrazinyl)propoxy]benzonitrile수율 48.8%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

10 ml of a 1.2M solution of butyllithium in n-hexane were added to a solution of 1.68 ml of diisopropylamine in 10 ml of tetrahydrofuran while stirring at -78° C. under a nitrogen atmosphere. The solution was stirred for a further 15 minutes and then 0.94 g of 2-methylpyrazine in 20 ml of tetrahydrofuran was added. The solution was allowed to warm to 20° C. and was stirred for 1 hour. The solution was then cooled to -78° C., 2.33 g of ethyl 2-(4-cyanophenoxy)-2-methylpropionate in 30 ml of tetrahydrofuran were added and the mixture was allowed to warm to 20° C. The mixture was treated with 20 ml of water and the solvent was removed by evaporation. The residue was chromatographed on silica gel using ethyl acetate for the elution to give 1.37 g of 4-[1,1-dimethyl-2-oxo-3-(2-pyrazinyl)propoxy]benzonitrile.

후처리

  1. stirringThe solution was stirred for a further 15 minutes
  2. temperatureto warm to 20° C.
  3. stirringwas stirred for 1 hour
  4. temperatureThe solution was then cooled to -78° C.
  5. temperatureto warm to 20° C
  6. customthe solvent was removed by evaporation
  7. customThe residue was chromatographed on silica gel
  8. washfor the elution

출처 및 근거

ORD 기록
ord-e0f5e1257ee74956bea6c01036f91f65
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04971982

반응 노트

불러오는 중…