Acetic Acid → Ethyl 2-cyano-3-ethoxy-2-butenoate

HRID 1050852

Reaction equation

HRID 1050852 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([C:11](CC)(CC)[C:12]([O-:15])([O-])[O-])C.[C:20](O)(=O)[CH3:21]>>[C:1]([C:3](=[C:20]([O:15][CH2:12][CH3:11])[CH3:21])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 21875354Triethylorthoaceate

Product 1

HCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoate

Conditions

Temperature
125 °C

Procedure

A mixture of ethyl 2-cyanoacetate (120 g, 1.06 mol) and triethylorthoacetate (354 g, 2.12 mol) in glacial acetic acid (33 g, 0.53 mol) was heated at 120-130° C. overnight. The mixture was concentrated under vacuum to provide crude ethyl 2-cyano-3-ethoxybut-2-enoate. The residue was carried into the next reaction without further purification assuming 100% conversion.

Workup

  1. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-d7423d3c30894700ac42e3a3b94019ef
Source dataset
uspto-grants-2016_07
Patent number
US09387202B2

Linked notes

Loading…