Propargyl alcohol → 3-Quinolin-3-ylprop-2-yn-1-ol

Participants

Reaction Steps

To a dry 2-L three-necked flask previously purged with nitrogen, was charged 3-bromoquinoline (118.77 g, 570 mmol), propargyl alcohol (71.9 g, 1.28 mol, 2.25 equiv), triethylamine (1500 mL), copper(I) iodide (3.62 g, 19 mmol, 0.033 equiv) and dichlorobis(triphenylphosphine) palladium(II) (6.67 g, 9.5 mmol). The resulting mixture was mechanically stirred and heated to reflux for 3 hours. Upon cooling, the triethylamine solution was filtered and washed with triethylamine (300 mL). The filtrate was then concentrated under reduced pressure to provide solids which were suspended in 5% aq. NaHCO3 (600 mL) and extracted with ethyl acetate (1×600 mL). The solids which were left after filtration were treated in the same manner (i.e., suspend in aq. 5% NaHCO3 and extracted with ethyl acetate). The combined ethyl acetate extracts were stirred with silica gel (15 g) and decolorizing carbon (3 g) before being filtered through a bed of diatomaceous earth. The filtrate was concentrated under reduced pressure to provide a tan colored solid which was dried in the vacuum oven at 45° C. overnight. The 3-(3-quinolyl)-2-propyn-1-ol was thus isolated. 92.14 g, 88.3% yield. MS(Cl): (M+H)+ at 184; NMR (300 MHz CDCl3) δ: 4.58 (s, 2H), 4.70 (s, broad, 1H), 7.57 (m,1H), 7.70 (m, 1H), 7.77 (d, 1H), 8.10 (d, 1H), 8.10 (s, H), 9.05 (s, 1H).

Provenance & Evidence