Ethyl propiolate → Ethyl 3-(pyrrolidin-1-yl)acrylate

HRID 443723Notes

Reaction equation

HRID 443723 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>C1C=CC=CC=1>[N:8]1([CH:3]=[CH:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 31268Pyrrolidine

Product 1

HCID 2748620Ethyl 3-(pyrrolidin-1-yl)acrylateYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 29.43 g of ethyl propiolate (0.30 mol) in 200 ml of benzene was held at 25° in a water bath with magnetic stirring. A solution of 21.34 g of pyrrolidine in 50 ml of benzene was added dropwise over a period of 45 minutes, during which time the temperature rose to 35°. The clear brown solution was stirred overnight and the solvent removed under reduced pressure at 55°. The residue was distilled under pressure to give 35.05 g of yellow oil, boiling point 110° (0.4 torr), which crystallized upon standing. The yellow solid was recrystallized from petroleum ether to give 31.36 (62%) of yellowish platelets, m.p. 37.5°-39.5°.

Workup

  1. customrose to 35°
  2. customthe solvent removed under reduced pressure at 55°
  3. distillationThe residue was distilled under pressure

Sources & evidence

ORD record
ord-32ef0926e5ed4c80b96e3869af979804
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Reaction notes

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