128538-83-0Relevant academic research and scientific papers
2,2,4-TRICHLOROBUTANAL: AN INVITATION TO THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS
Buyck, L. De,Menke, N.,Schamp, N.
, p. 121 - 126 (2007/10/02)
The title aldehyde (1) was obtained in 69percent isolated yield by chlorination of 4-chlorobutanol in the presence of dimethylformamide. 3,3-Dichloro-2-hydroxytetrahydrofuran (3a) or the 2-alkoxyderivatives 3b and 3c were produced by treating the hydrate 2a or the hemiacetals 2b and 2c resp. with base.With aqueous ammonia 1 rapidly formed the hemiaminal which then slowly afforded 3,3-dichloro-1-pyrroline (4).In a rapid reaction with primary alkylamines 1 was converted to N-alkyl-3,3-dichloro-2-hydroxypyrrolidines (5).The 2-hydroxyl group in 5 was reversibly exchanged in the presence of alcohols or amines. 5 were converted to N-alkyl-3,3-dichloro-1-pyrrolinium salts by an excess of trifluoroacetic acid.
