Benzyl Chloride → 1-Benzylcyclopropanecarbonitrile

HRID 274121

反応式

HRID 274121 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1([C:16]#[N:17])[CH2:15][CH2:14]1.[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CCCCCC.O1CCCC1>[C:19]1([CH2:18][C:13]2([C:16]#[N:17])[CH2:15][CH2:14]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

8

反応物 4

HCID 7503Benzyl ChlorideHCID 7912DiisopropylamineHCID 79637CyclopropanecarbonitrileHCID 178418339Butyllithium

生成物 1

HCID 223466521-Benzylcyclopropanecarbonitrile収率 53.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

To a mixture under nitrogen of 26.3 g (260 mmoles) of diisopropylamine and 300 ml of tetrahydrofuran cooled to -75° C., there is added dropwise 125 ml (200 mmoles) of n-butyllithium in a 1.6M hexane solution, then 13.4 g (200 mmoles) of commercial cyclopropanecarbonitrile and finally 25.3 g (200 mmoles) of benzyl chloride. The reaction mixture is stirred 2 hours at -70° C. then 2 days at 20° C. 4 ml of water is added, before washing the reaction mixture with water saturated with NaCl. The organic phase dried over Na2SO4 is concentrated to give a brown liquid, which is purified by distillation. There is obtained 16.8 g (yield=53.5%) of a colorless liquid. b.p.13 =140°-8° C. A new distillation gives a colorless liquid. b.p.0.3 =64°-8° C.

後処理

  1. custom2 days
  2. customat 20° C
  3. washbefore washing the reaction mixture with water saturated with NaCl
  4. dry with materialThe organic phase dried over Na2SO4
  5. concentrationis concentrated
  6. customto give a brown liquid, which
  7. distillationis purified by distillation

出典と根拠

ORDレコード
ord-089a551bd8ae42dc9d7c960eb6247f10
出典データセット
uspto-grants-1995_02
特許番号
US05387709

関連ノート

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