Ethylene Glycol → 2-hydroxyethyl 3-(N-vinylformamido)propionate

HRID 2386

Reaction equation

HRID 2386 reaction equation
[CH:1]([N:3]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]=[O:5])=[CH2:2].C(O)C[OH:15].C[O-].[Na+].C(O)C>CO>[CH:1]([N:3]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH2:12][OH:15])=[O:9])[CH:4]=[O:5])=[CH2:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 702EthanolHCID 10942334Sodium MethoxideHCID 19690337ethyl 3-(N-vinylformamido)propionate

Product 1

HCID 196903422-hydroxyethyl 3-(N-vinylformamido)propionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

The apparatus of Example 2 was charged with 17.1 grams (0.1 mol) of ethyl 3-(N-vinylformamido)propionate, 6.2 grams (0.1 mol) of ethylene glycol, and 0.15 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 2 hours. No evolution of ethanol was observed during the reaction period. Heating for an additional hour at 135° C. also failed to generate a volatile coproduct which indicated no conversion to the desired product.

Workup

  1. temperatureHeating for an additional hour at 135° C.

Sources & evidence

ORD record
ord-9263fd3c38db4e7d8af1acf74087dcb3
Source dataset
uspto-grants-1998_03
Patent number
US05728878

Linked notes

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