Dimethylformamide dimethyl acetal → Ethyl 2-cyano-5-dimethylamino-3-methylpenta-2,4-dienoate

HRID 369455Notes

Reaction equation

HRID 369455 reaction equation
[C:1](=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:3])[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>C(O)C>[C:10]([C:4](=[C:1]([CH3:2])[CH:3]=[CH:14][N:15]([CH3:17])[CH3:16])[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1365732-Cyano-3-methyl-but-2-enoic acid ethyl ester

Product 1

HCID 54385987Ethyl 2-cyano-5-dimethylamino-3-methylpenta-2,4-dienoateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 127.7 g (0.839 mole) of ethyl isopropylidenecyanoacetate (4) and 100 g (0.839 mole) of N.N-dimethylformamide dimethyl acetal in 500 mL of ethanol was refluxed for 24 hours. The ethanol was removed under reduced pressure to give 124 g (100%) of a dark oil.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe ethanol was removed under reduced pressure

Sources & evidence

ORD record
ord-0e34adf709a642c9b585539b628c6eb3
Source dataset
uspto-grants-2000_10
Patent number
US06136982

Reaction notes

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