Acetone → Ethyl acetate hexane

Participants

Reaction Steps

3-([1,1′-Biphenyl]-3-yl)-6,7-dimethoxyisoquinoline-1-carboxaldehyde (160 mg) in 7 mL ethanol was treated slowly with NaBH4 (50 mg, 3 eq.) at room temperature. Reaction was stirred for 1 hour then 2 mL acetone was added and solution was filtered through filter paper. Filtrate was concentrated then re-dissolved in DCM and washed with H2O. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 50% EtOAc/hexane yielding product as a yellow solid (98 mg, 61% yield). 1H NMR (400 MHz) (CDCl3) δ 8.36-8.35 (m, 1H), 8.13-8.11 (m, 1H), 7.98 (s, 1H), 7.73 (d, J=8 Hz, 2H), 7.68-7.66 (m, 1H), 7.60 (t, J=16 Hz, 1H), 7.51 (t, J=16 Hz, 2H), 7.42 (t, J=12 Hz, 1H), 7.22 (s, 1H), 7.09 (s, 1H), 5.35 (bs, 1H), 5.32 (s, 2H), 4.08 (s, 3H), 4.07 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ 154.65, 141.81, 141.21, 129.19, 128.82, 127.44, 127.29, 127.25, 125.55, 125.51, 119.82, 115.35, 105.87, 101.29, 61.41, 56.14, 56.09.

Provenance & Evidence