Triphenylphosphine → 6-(3-Fluoropropoxy)-indan-1-one

Participants

Reaction Steps

To a solution of 6-hydroxy-2,3-dihydro-1H-inden-1-one (3.0 g, 20 mmol) in THF (140 mL) were 3-fluoropropan-1-ol (1.67 mL, 22.3 mmol), triphenylphosphine (7.97 g, 30.4 mmol) and diisopropyl azodicarboxylate (5.98 mL, 30.4 mmol) added. The mixture was stirred at r.t. for two days. More 3-fluoropropanol (0.5 mL) was added and the mixture was heated to 45° C. After 2 h the mixture was concentrated, and the crude product was purified by flash chromatography using 0-20% EtOAc in heptane as eluent, affording 3.42 g (81% yield) of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.12-2.26 (m, 2H), 2.68-2.76 (m, 2H), 3.04-3.12 (m, 2H), 4.14 (t, 2H), 4.61 (t, 1H), 4.70 (t, 1H), 7.17-7.22 (m, 2H), 7.38 (d, 1H); MS (EI) m/z 208 M.

Provenance & Evidence