Org. Synth. 1953, 33, 35
DOI: 10.15227/orgsyn.033.0035
ETHYL α-(1-PYRROLIDYL)PROPIONATE
[1-Pyrrolidineacetic acid, α-methyl-, ethyl ester]
Submitted by Robert Bruce Moffett
1
Checked by N. J. Leonard and S. Gelfand.
1. Procedure
A 1-l. three-necked round-bottomed flask is placed on a steam bath and fitted with a stirrer, reflux condenser, and dropping funnel. A solution of 181 g. (1 mole) of ethyl α-bromopropionate in 200 ml. of benzene is placed in the flask (Note 1), and 148 g. (2.1 moles) of pyrrolidine (Note 2) is added slowly with stirring at such a rate that the solvent refluxes gently. When the addition is complete (about 1 hour is required), the mixture is heated under reflux for 1 hour. After being cooled, the mixture is poured into about 500 ml. of ice water and acidified with dilute hydrochloric acid. The aqueous layer is separated, washed once with ether, and made strongly basic with cold 40% sodium hydroxide solution. The basic ester is extracted with four 200-ml. portions of ether. The ether extracts are combined, washed with 100 ml. of water, and dried over anhydrous potassium carbonate. The drying agent is removed by filtration and the ether by distillation. The residue is distilled under reduced pressure through a short fractionating column; b.p. 84°/12 mm. (95–96°/19 mm., 99.5–100.5°/23 mm., 104–105°/30 mm.); nD20 1.4478, nD25 1.4450; d425 0.9724. The yield is 137–156 g. (80–91%).
2. Notes
1.
The yield of product is lowered appreciably if the solution is preheated before addition of the
pyrrolidine.
2.
Pyrrolidine is obtainable from E. I. du Pont de Nemours and Company, Electrochemicals Division, Niagara Falls, New York.
3. Discussion
Ethyl α-(1-pyrrolidyl)propionate has been prepared by the reaction of
pyrrolidine with
ethyl α-bromopropionate.
2
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
potassium carbonate (584-08-7)
hydrochloric acid (7647-01-0)
Benzene (71-43-2)
ether (60-29-7)
sodium hydroxide (1310-73-2)
ethyl α-bromopropionate (535-11-5)
pyrrolidine (123-75-1)
Ethyl α-(1-pyrrolidyl)propionate,
1-Pyrrolidineacetic acid, α-methyl-, ethyl ester (26846-86-6)
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