Acetone → Ethyl acetate hexane

Participants

Reaction Steps

3-(3′-(tert-Butyl)-[1,1′-biphenyl]-3-yl)-6,7-dimethoxyisoquinoline-1-carbaldehyde (52 mg) in 4 mL ethanol was treated slowly with NaBH4 (14 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 oil (27 mg, 52% yield). 1H NMR (400 MHz) (CDCl3) δ 8.24 (t, J=4 Hz, 1H), 8.03-8.01 (m, 1H), 7.88 (s, 1H), 7.62 (m, 1H), 7.57-7.55 (m, 1H), 7.51 (t, J=12 Hz, 1H), 7.45-7.42 (m, 1H), 7.36-7.35 (m, 2H), 7.12 (s, 1H), 6.98 (s, 1H), 5.39 (bs, 1H), 5.12 (s, 2H), 3.99 (s, 3H), 3.98 (s, 3H), 1.33 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 154.60, 153.16, 151.69, 150.40, 147.62, 142.51, 141.06, 139.64, 133.80, 129.14, 128.55, 127.49, 125.67, 125.47, 124.61, 124.52, 124.46, 119.79, 115.38, 105.87, 101.22, 61.39, 56.13, 34.88, 31.47.

Provenance & Evidence