The goal of this project was to add a fluorine to 1-indanone and then to reduce it to 2-fluoro-1-indanol. The plan was to first add a fluorine to 1-indanone by using Selectfluor. To do so, acetonitrile and calcium hydride were refluxed with the ketone overnight. Following this, Selectfluor was added at room temperature. <sup>1</sup>H NMR with peaks at 7.78 (d), 7.65 (t), 7.45-7.40 (m), 7.25 (s), 5.35 (q), 5.28 (s), 5.17 (dd), 3.78-3.55 (m), 3.28 (d), 3.20 (t), 3.14 (d), 2.0 (m) ensured that 2-fluoro-1-indanone was produced. Following this, the 2-fluoro-1-indanone previously made was then reduced by L-Selectride and Tetrahydrofuran. Both reducing agents were added to the fluorinated ketone and stirred at -78 °C under nitrogen. 37% was yielded. Key spectra included <sup>19</sup>F NMR that showed a peak at -201.6 ppm which correlates to the cis isomer.

Fluorination and reduction of 1-indanone as a method to study carbon-fluorine hydrogen bonding

2019 Spring National Meeting

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