FACILE SYNTHESIS OF UHLES KETONE BY THE REGIOSELECTIVE FRIEDEL-CRAFTSCYCLIZATION

Authors
TERANISHI K YAHASHI S NAKATSUKA S GOTO T
Citation
K. Teranishi et al., FACILE SYNTHESIS OF UHLES KETONE BY THE REGIOSELECTIVE FRIEDEL-CRAFTSCYCLIZATION, Synthesis, (5), 1995, pp. 506-508
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
5
Year of publication
1995
Pages
506 - 508
Database
ISI
SICI code
0039-7881(1995):5<506:FSOUKB>2.0.ZU;2-H
Abstract
A facile synthesis of Uhle's ketone starting from 3-(indol-3-yl)propio nic acid is described. Tn the presence of a large amount of donor-acce ptor complex, the species generated from chloroacetyl chloride and alu minum chloride, 3-(1-trimethylacetylindol-3-yl)propionyl chloride reac ts regioselectively to give trimethylacetyl derivative of Uhle's keton e in 78 % yield. Deacylation of trimethylacetyl group gives Uhle's ket one in an overall yield of 67 %.