Diisopropylamine → 2-(4-Methoxyphenyl)propanenitrile

HRID 1011491노트

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HRID 1011491 반응식
[Li]CCCC.C(N[CH:10]([CH3:12])[CH3:11])(C)C.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18](C#N)=[CH:17][CH:16]=1.BrCC1C2C=CC(O[Si](C(C)(C)C)(C)C)=CC=2O[N:26]=1>O.C1COCC1>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:10]([CH3:11])[C:12]#[N:26])=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 701294-MethoxybenzonitrileHCID 231171383-(Bromomethyl)-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazoleHCID 178418339Butyllithium

생성물 1

HCID 122976702-(4-Methoxyphenyl)propanenitrile수율 28%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매4회

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온도
-20 °C

실험 절차

A solution of n-BuLi 2.0M in THF (9.7 mmoles) was slowly added to a solution of diisopropylamine (1.3 ml, 1.05 eq) and dry THF (10 ml) at −20° C. under N2. The mixture was stirred for 30 min at −20° C., then 4-methoxybenzonitrile (1.3 g, 8.8 mmoles) and dry THF (10 ml) were slowly added at −78° C. The mixture was stirred for 30 min at −78° C., then 3-(bromomethyl)-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole (3 g, 8.8 mmoles) and dry THF (10 ml) were slowly added. The mixture was then stirred for 30 min at room temperature, poured into water, extracted with AcOEt, dried over Na2SO4, and purified by flash chromatography (AcOEt/Heptane 2/8 with 0.1% TEA) to give 3-(6-[(tert-butyl)dimethylsilyl)oxy]-1,2-benzisoxazol-3-yl)-2-(4-methoxyphenyl) propanenitrile (1 g, 28%).

후처리

  1. stirringThe mixture was stirred for 30 min at −78° C.
  2. stirringThe mixture was then stirred for 30 min at room temperature
  3. extractionextracted with AcOEt
  4. dry with materialdried over Na2SO4
  5. custompurified by flash chromatography (AcOEt/Heptane 2/8 with 0.1% TEA)

출처 및 근거

ORD 기록
ord-e449499fc849420492fe94fc6ae8946e
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977364B2

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