Methyl Acrylate → 6'-(3-Fluoropropoxy)-4-hydroxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one

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The title compound was prepared following the method described for Intermediate 17 and in a subsequent step the method described for Intermediate 18, starting from 6-(3-fluoropropoxy)-2,3-dihydro-1H-inden-1-one (Intermediate 20, 3.16 g, 15.2 mmol) and methyl acrylate (3.01 mL, 33.4 mmol). The product was purified by flash chromatography (0-100% EtOAc in heptane) to afford the title compound as a 2:1 mixture of diastereomers (0.910 g, 32% yield). 1H NMR (500 MHz, CDCl3) δ ppm 1.43-1.52 (m, 3 H) 1.74-1.85 (m, 2 H) 1.95 (td, 1 H) 2.14-2.24 (m, 2 H) 2.93-3.02 (m, 2 H) 3.73-3.80 (m, 1 H) 4.10-4.16 (m, 2 H) 4.61 (t, 1 H) 4.70 (t, 1 H) 7.18-7.22 (m, 2 H) 7.31-7.38 (m, 1 H); MS (ES+) m/z 293.09 [M+H]+.

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