Pyrrolidine → Prop-2-en-1-yl 3-(pyrrolidin-1-yl)but-2-enoate

HRID 1109450Notes

Reaction equation

HRID 1109450 reaction equation
[C:1]([O:7][CH2:8][CH:9]=[CH2:10])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[N:11]1([C:3]([CH3:5])=[CH:2][C:1]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 70701Allyl acetoacetate

Product 1

HCID 54524772Prop-2-en-1-yl 3-(pyrrolidin-1-yl)but-2-enoateYield 46.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Allyl acetoacetate (68.4 ml, 0.5 mol) was added to pyrrolidine (41.6 ml, 0.5 mol) in 150 ml of toluene. An exotherm was noted. The mixture was heated at reflux for 3 hours, cooled, and stripped of toluene to yield 45 g of title product as a pale yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled

Sources & evidence

ORD record
ord-c99f0792fdc242faa701d85b2754e09c
Source dataset
uspto-grants-1994_06
Patent number
US05321020

Reaction notes

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