Water → Ethyl 1-cyanocyclopropanecarboxylate

HRID 512131

Reaction equation

HRID 512131 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-501787d574114debbb6ecb65bb37e02b
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Linked notes

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