Water → Ethyl 1-cyanocyclopropanecarboxylate

HRID 512131

反応式

HRID 512131 の反応式
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].Br[CH2:10][CH2:11]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1([C:6]#[N:7])[CH2:11][CH2:10]1)=[O:8])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

生成物 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylate収率 72%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A suspension of cyano-acetic acid ethyl ester (11.3 g, 0.1 mol), 1,2-Dibromo-ethane, Na4(n-Bu)4Br and K2CO3 in DMF (100 mL) was heated to 80° C. overnight. The mixture was poured into water (600 mL) and extracted with EtOAc (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4, concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (petroleum ether: EtOAc=10:1˜5:1) to give 1-cyano-cyclopropanecarboxylic acid ethyl ester (10 g, yield: 72%). 1H NMR (CDCl3 400 MHz): δ4.21 (q, J=7.2 Hz, 2H), 1.65-1.61 (m, 2H), 1.58-1.55 (m, 2H), 1.28 (t, J=7.2 Hz, 3H).

後処理

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product, which
  6. customwas purified by column chromatography on silica gel (petroleum ether: EtOAc=10:1˜5:1)

出典と根拠

ORDレコード
ord-501787d574114debbb6ecb65bb37e02b
出典データセット
uspto-grants-2015_08
特許番号
US09102591B2

関連ノート

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