3-Fluoro-1-propanol → 6-(3-Fluoropropoxy)-indan-1-one

Participants

Reaction Steps

The title compound (7.90 g, 94% yield) was prepared following the procedure for Intermediate 16, starting from 6-hydroxy-2,3-dihydro-1H-inden-1-one (5.98 g, 40.4 mmol) and 3-fluoropropan-1-ol (3.34 mL, 44.4 mmol). Additional 3-fluoropropan-1-ol (1.0 mL, 13.3 mmol) was added after stirring overnight to drive the reaction to completion. 1H NMR (500 MHz, CDCl3) δ ppm 2.20 (m, 2 H) 2.73 (m, 2 H) 3.08 (m, 2 H) 4.14 (t, 2 H) 4.61 (t, 3 H) 4.70 (t, 1 H) 7.21 (m, 2 H) 7.38 (d, 1 H); MS (ES+) m/z 208 [M+H]+.

Provenance & Evidence