Ethylamine → Methyl N-ethyl-beta-alaninate
Reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH2:7]([NH2:9])[CH3:8]>CO>[CH3:6][O:5][C:1](=[O:4])[CH2:2][CH2:3][NH:9][CH2:7][CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Methyl acrylate (5.22 g, 60.6 mmol) is dissolved in methanol (20 mL) and cooled to −20° C. Ethylamine (2 M in tetrahydrofuran, 47 mL, 94 mmol) is added via addition funnel and the reaction is allowed to stir at −20° C. for 2 hours. Solvents were then removed in vacuo and the residue is distilled under reduced pressure to afford the title compound as a colorless liquid (2.41 g, 30% yield). 1H NMR (CDCl3) 1.11 (t, 3H, J=7.02 Hz), 2.53 (t, 2H, J=6.58 Hz), 2.66 (q, 2H, J=7.02 Hz), 2.89 (t, 2H, J=6.58 Hz), 3.69 (s, 3H).
Workup
- customSolvents were then removed in vacuo
- distillationthe residue is distilled under reduced pressure
Sources & evidence
- ORD record
- ord-763e89253a5846439d85d72ba124a2f8
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362063B2
Reaction notes
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