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Synthesis 1995; 1995(5): 506-508
DOI: 10.1055/s-1995-3943
short paper
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Facile Synthesis of Uhle’s Ketone by the Regioselective Friedel-Crafts Cyclization

Katsunori Teranishi, Syunzi Hayashi, Shin-ichi Nakatsuka* , Toshio Goto
  • *School of Agriculture, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
31 December 2000 (online)

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A facile synthesis of Uhle’s ketone starting from 3-(indol-3-yl)propionic acid is described. In the presence of a large amount of donor-acceptor complex, the species generated from chloroacetyl chloride and aluminum chloride, 3-(1-trimethylacetylindol-3-yl)propionyl chloride reacts regioselectively to give trimethylacetyl derivative of Uhle’s ketone in 78% yield. Deacylation of trimethylacetyl group gives Uhle’s ketone in an overall yield of 67%.

Efficient synthesis of Uhle’s ketone is described

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