Triphenylphosphine → 5-((4-Phenyl-5-trifluoromethyl-2-thienyl)methoxy)-1-indanone

Participants

Reaction Steps

A solution of 0.25 g (0.97 mmol) of 2-hydroxymethyl-4-phenyl-5-trifluoromethyl-thiophene (from Step D), 0.17 g (1.16 mmol) of 5-hydroxy-1-indanone and 0.31 g (0.16 mmol) of triphenylphosphine in 2.5 mL of THF at 0° C. was treated with 0.18 mL (0.16 mmol) of diethylazodicarboxylate. The resulting mixture was warmed to rt, and stirred for 2 h. The reaction was loaded onto silica gel and eluted with 33% ethyl acetate/hexanes to give 0.35 g (0.90 mmol, 78%) of the title compound as a white solid: 1H NMR (500 MHz) δ 7.76 (d, J=8.3 Hz, 1H), 7.42–7.47 (m, 5H), 7.14 (s, 1H), 7.01–7.03 (m, 2H), 5.34 (s, 2H), 3.15 (t, J=5.9 Hz, 2H), 2.72 (t, J=6.0 Hz, 2H); ESI-MS 388.9 (M+H).

Provenance & Evidence