HCID 57172719, compound → HCID 18475323, compound

HRID 1386496Notes

Reaction equation

HRID 1386496 reaction equation
[C:1]([C:3](=[CH:9][CH:10]1[CH2:12][CH2:11]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH3:13][Mg]Br>[Cu]I.C(OCC)C>[C:1]([CH:3]([CH:9]([CH:10]1[CH2:11][CH2:12]1)[CH3:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 2

HCID 57172719HCID 57172719, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18475323HCID 18475323, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

7.3 g (44 mmol) of ethyl 2-cyano-3-cyclopropyl-2-propenoate and 0.15 g of copper(I) iodide were introduced into 100 ml of dry diethyl ether. 16.9 ml of etheric 3 M methylmagnesium bromide solution (51 mmol) was then added dropwise at reflux temperature, and the mixture was subsequently stirred for 14 hours at room temperature. For working-up, the mixture was poured into 300 ml of ice-water and stirred for 10 minutes. The aqueous phase was separated off and washed with ether. The combined organic phase [sic] were washed with saturated sodium chloride solution, dried with sodium sulfate and concentrated. The residue was subjected to fractional distillation in vacuo. This gave 4.9 g (yield 61%) of ethyl 2-cyano-3-cyclopropylbutanoate (b.p. 90° C./2 mbar).

Workup

  1. temperatureat reflux temperature
  2. stirringstirred for 10 minutes
  3. customThe aqueous phase was separated off
  4. washwashed with ether
  5. washThe combined organic phase [sic] were washed with saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. distillationThe residue was subjected to fractional distillation in vacuo

Sources & evidence

ORD record
ord-633acd198a2843e19fd04d3dba43f4b9
Source dataset
uspto-grants-2001_07
Patent number
US06265447B1

Reaction notes

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