Ammonia → (2-Methyl-1,3-dioxolan-2-yl)methyl (Z)-3-aminobut-2-enoate

HRID 543553Notes

Reaction equation

HRID 543553 reaction equation
[NH3:1].[C:2]([O:8][CH2:9][C:10]1([O:15][CH2:14][CH2:13][O:12]1)[CH3:11])(=[O:7])[CH2:3][C:4]([CH3:6])=O>CO>[NH2:1]/[C:4](/[CH3:6])=[CH:3]\[C:2]([O:8][CH2:9][C:10]1([O:15][CH2:14][CH2:13][O:12]1)[CH3:11])=[O:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13239718(2-Methyl-1,3-dioxolan-2-yl)methyl 3-oxobutanoate

Product 1

HCID 86739392(2-Methyl-1,3-dioxolan-2-yl)methyl (Z)-3-aminobut-2-enoateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas was passed through a mixture of 19 g of 2,2-ethylenedioxypropyl acetoacetate and 100 ml of methanol for 2.5 hours under ice-cooling while stirring. The solvent was then distilled off and the residue was distilled under reduced pressure to obtain 16 g (84% yield) of 2,2-ethylenedioxypropyl 3-aminocrotonate as a pale yellow oil having a boiling point of 120° C. (5 mmHg).

Workup

  1. temperaturecooling
  2. distillationThe solvent was then distilled off
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-09e295f16601429f88341577c4aba310
Source dataset
uspto-grants-1984_05
Patent number
US04446325

Reaction notes

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