Ethyl cyanoacetate → ethyl 1-cyanocyclobutanecarboxylate

HRID 2366734Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].Br[CH2:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>>[C:6]([C:5]1([C:4]([O:3][CH2:1][CH3:2])=[O:8])[CH2:12][CH2:11][CH2:10]1)#[N:7]

Participants

Reactant 3

HCID 7764Ethyl cyanoacetate

HCID 80011,3-Dibromopropane

HCID 11430Potassium Carbonate

Product 1

HCID 275343ethyl 1-cyanocyclobutanecarboxylate

Procedure

The method described in Part A of Example 64 was used to treat ethylcyanoacetate (45 mL, 420 mmol) with 1,3-dibromopropane (51 mL, 510 mmol) and potassium carbonate (146 g, 1.06 mol) to provide ethyl 1-cyanocyclobutanecarboxylate as an orange oil containing about 15 mole % 1,2-dibromopropane.

Sources & evidence

ORD record: ord-6359fe9200cd4af690971d5202f0ebd7
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697873B2

Reaction notes

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