Methyl propiolate → HCID 86681478, compound

HRID 339990Notes

Reaction equation

HRID 339990 reaction equation
[NH2:1]/[C:2](/[CH3:9])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10]([O:14][CH3:15])(=[O:13])[C:11]#[CH:12]>>[NH2:1]/[C:2](=[C:3](\[C:4]([O:6][CH2:7][CH3:8])=[O:5])/[CH:12]=[CH:11]/[C:10]([O:14][CH3:15])=[O:13])/[CH3:9]

Participants

3

Reactant 2

HCID 13536Methyl propiolateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 1

HCID 86681478HCID 86681478, compoundYield 93.8%

Conditions

Temperature
110 °C

Procedure

Ethyl (2Z)-3-aminobut-2-enoate (6.46 g, 50.0 mmol) and methyl propiolate (4.20 g, 50.0 mmol) were mixed in one 100 mL flask, and the mixture was stirred at 110° C. for 10 hrs. The reaction mixture was cooled to room temperature and recrystallized with methanol to give 10 g (93% yield) of the pure product. LC-MS found: 214.2.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customrecrystallized with methanol

Sources & evidence

ORD record
ord-67075832b21741ac8627a8bdcca638b1
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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