Aromatische Spirane, 22. Mitt.: Darstellung von Cyclopenteno-4,5-indan-1-on und 2-Carboxymethyl-bzw. 4-Chlormethyl-indan als Synthone für Synthesen von anellierten 2,2′-Spirobiindanonen |
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Authors: | M. Melmer H. Neudeck |
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Affiliation: | (1) Institut für Organische Chemie, Universität Wien, A-1090 Wien, Österreich |
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Abstract: | Summary The title compounds were prepared as follows:tert.-butyl-indane (10) was formylated to give a 72:28 mixture of the aldehydes23a and23b which were submitted to aKnoevenagel-Doebner condensation to afford the cinnamonic acids24. From the mixture, the pure stereoisomer24a was obtained by one crystallization in 57% yield. Its methylester27a could be quantitatively dealkylated to the methylester8 by treatment with AlCl3 in toluene. Cyclization to the indanone9 was then performedvia the propionic acid7 with polyphosphoric acid in 95% yield. From9 the carboxymethyl derivative30 was obtained by treatment with dimethylcarbonate and NaH. The second synthone 4-chlormethyl-indane (19) was prepared from the corresponding alcohol18 (in 82% yield) which in turn could be obtained from methylester17 by reduction with LiAlH4. The latter was accessible in 75% yield by dealkylation of ester13.Herrn Prof. Dr.K. Kratzl mit besten Wünschen zum 80. Geburtstag gewidmet |
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Keywords: | Mono- and disubstituted Indanes Cyclopenteno-4,5-indan-1-one 1H NMR 13C NMR Mass spectra |
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