Diethyl Ether → 1-[(Oxiran-2-yl)methyl]-1H-pyrrole

A reaction mixture formed from 200 g of sodium hydroxide NaOH, 8.4 g of tetrabutylammonium hydrogensulfate, 200 ml of water and 125 ml of epichlorohydrin is stirred very vigorously at room temperature in a one liter reactor. 40 g of freshly distilled pyrrole are added dropwise while cooling the solution with a bath of ice-cold water in order to keep the temperature of the mixture between 15° and 20° C. The mixture is left stirring with a stream of nitrogen for 3 hours, 100 ml of ether are added in order to cause an aqueous phase and an organic phase to settle which are separated from each other. The aqueous phase is extracted twice with 100 ml of ether. The whole of the organic phase is washed with aqueous salt solution until neutrality, dried over a molecular sieve, filtered and distilled under vacuum. 58 g of N-glycidylpyrrole ##STR4## or a yield of 80%, are obtained. The product is characterized by 1H NMR and 13C NMR. Its purity is 93%; it is determined by liquid phase chromatography.

1. temperaturewhile cooling the solution with a bath of ice-cold water in order
2. customthe temperature of the mixture between 15° and 20° C
3. waitThe mixture is left
4. stirringstirring with a stream of nitrogen for 3 hours
5. customare separated from each other
6. extractionThe aqueous phase is extracted twice with 100 ml of ether
7. washThe whole of the organic phase is washed with aqueous salt solution until neutrality
8. customdried over a molecular sieve
9. filtrationfiltered
10. distillationdistilled under vacuum

ORD record

ord-4c07143c6565410d8ab59fc810fbb639

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE035802