A Practical Synthesis of N-p-Anisyl-N-methyl-amino-3-(9-anthryl)-propane: An Exciplex Fluorescence ‘Thermometer’

Abstract

A practical synthesis of N-p-anisyl-N-methyl-amino-3-(9-anthryl)-propane from 9-anthraldehyde is described. All the intermediates in this simple five step sequence are crystalline and simple re-crystallisation after each step allows the preparation of this exciplex fluorescence ‘thermometer’ molecule on a preparative scale without resort to chromatography.

Notes

Prices are from Aldrich 1996–97.

We encountered the same problem when hydrogenating ester 3 under these conditions. The over-reduced product of this reaction, methyl 3-(9,10-dihydro-9-anthryl)propanoate could be obtained very cleanly by the action of magnesium in methanol on ester 3.³²