Ethyl propiolate → HCID 53986483, compound

HRID 1647865Notes

Reaction equation

HRID 1647865 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[CH3:8][C:9]1([CH3:18])[NH:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:11](=[O:12])[CH2:10]1>C(O)C>[CH3:16][C:14]1([CH3:17])[CH2:13][C:11](=[O:12])[CH2:10][C:9]([CH3:18])([CH3:8])[N:15]1[CH:3]=[CH:2][C:1]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 132202,2,6,6-Tetramethyl-4-piperidone

Product 1

HCID 53986483HCID 53986483, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

54 g (0.55 mol) of ethyl propiolate were added dropwise to 78 g (0.50 mol) of triacetoneamine in 200 ml of ethanol at reflux, and the mixture was then stirred at this temperature for a further 4 hours. After cooling, the precipitated product was filtered off, thoroughly washed with petroleum ether and subsequently dried at 60° C. and under 0.1 mbar. 80 g (corresponding to a yield of 63%) of ethyl β-(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl)acrylate were obtained in the form of a colorless solid of melting point 145° C.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. filtrationthe precipitated product was filtered off
  4. washthoroughly washed with petroleum ether
  5. customsubsequently dried at 60° C. and under 0.1 mbar

Sources & evidence

ORD record
ord-c457906aed2a4e478f8e4f0fb4dda675
Source dataset
uspto-grants-1995_07
Patent number
US05434202

Reaction notes

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