Diisopropylamine → 2-(4-Methoxyphenyl)propanenitrile

HRID 1921273노트

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HRID 1921273 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-98b0d80879dc40fcb084236689d4eb1f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173679B2

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