Diisopropylamine → 2-(4-Methoxyphenyl)propanenitrile

HRID 1011491ノート

反応式

HRID 1011491 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 122976702-(4-Methoxyphenyl)propanenitrile収率 28%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
-20 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-e449499fc849420492fe94fc6ae8946e
出典データセット
uspto-grants-2011_07
特許番号
US07977364B2

反応ノート

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