Ethyl 2-cyano-3-ethoxy-2-butenoate → Ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate

HRID 1050853Notes

Reaction equation

HRID 1050853 reaction equation
[C:1]([C:3](=[C:9]([O:11][CH2:12][CH3:13])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[C:1]([C:3](=[C:9]([O:11][CH2:12][CH3:13])[CH:10]=[CH:16][N:17]([CH3:19])[CH3:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

3

Reactant 2

HCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 54113151Ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 2-cyano-3-ethoxybut-2-enoate (194 g theory, 1.06 mol) and N,N-dimethylformamide dimethyl acetal (160 g, 1.325 mol) was heated at 70° C. for 2 h. The mixture was concentrated under high vacuum to provide crude ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate. The residue was used directly without further purification.

Workup

  1. concentrationThe mixture was concentrated under high vacuum

Sources & evidence

ORD record
ord-eb0270499e8f4d27b604596e4c11964b
Source dataset
uspto-grants-2016_07
Patent number
US09387202B2

Reaction notes

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