Water → Ethyl 1-cyanocyclopropanecarboxylate

HRID 512131

반응식

HRID 512131 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylate수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-501787d574114debbb6ecb65bb37e02b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102591B2

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