Ethyl cyanoacetate → ethyl 1-cyanocyclobutanecarboxylate

HRID 2242383Notes

Reaction equation

C(CC(OCC)=O)#N.BrCCCBr.[CH2:14]([O:16][C:17]([C:19]1([C:24]#[N:25])[CH2:23][CH2:22][CH2:21]C1)=[O:18])[CH3:15]>>[CH2:14]([O:16][C:17]([C:19]1([C:24]#[N:25])[CH2:23][CH2:22][CH2:21]1)=[O:18])[CH3:15]

Participants

Reactant 3

HCID 7764Ethyl cyanoacetate

HCID 80011,3-Dibromopropane

HCID 15688760Ethyl 1-cyanocyclopentane-1-carboxylate

Product 1

HCID 275343ethyl 1-cyanocyclobutanecarboxylateYield 67%

Procedure

1-Cyano-cyclobutanecarboxylic acid ethyl ester was prepared from ethyl cyanoacetate (10.0 g, 88.4 mmol) and 1,3-dibromopropane (8.9 ml, 88.5 mmol) in the same manner as 1-cyano-cyclopentanecarboxylic acid ethyl ester giving 1-cyano-cyclobutanecarboxylic acid ethyl ester as a yellow oil (9.03 g, 67%).

Sources & evidence

ORD record: ord-d131af1f64c641d999c708c46764bb30
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671080B2

Reaction notes

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