Ethyl cyanoacetate → HCID 19979312, compound

HRID 1461736Notes

Reaction equation

[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1Cl)=[O:11]>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH2:9][CH:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 7764Ethyl cyanoacetate

HCID 27365072'-Chloro-4'-fluoroacetophenone

Product 1

HCID 19979312HCID 19979312, compound

Procedure

The compound of formula III, when n and p are equal to 1 and q is equal to 1, is prepared from ethyl cyanoacetate and 2-chloro-4-fluoroacetophenone. The ethyl 2-(4-fluorophenacyl)cyanoacetate thereby obtained is then reacted with anhydrous ethylene glycol to obtain 2-[2-(2-cyanoethoxycarbonyl) ethyl]-2-(4-fluorophenyl)-l,3-dioxolane. Hydrogenation of the latter compound leads to 2-[2-(2-aminomethylethoxycarbonyl)ethyl]-2-(4-fluorophenyl)- 1,3-dioxolane, which is reacted with methylmagnesium iodide to obtain 2 (4-fluorophenyl)-2-[(2-oxo-azetidin-3-yl) methyl]dioxolane. This compound is subjected to the action of lithium aluminum hydride to obtain the expected compound.

Sources & evidence

ORD record: ord-186e2f0e207049ce8b54ed62598b7a79
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05077288

Reaction notes

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