Tetrahydrofuran → HCID 22403953, compound

Participants

Reaction Steps

In a 100-mL round-bottom flask, a total of 1.9 g (13 mmol) of 2-formylindole and 780 mg (26 mmol) of NaH (80% dispersion in mineral oil) was stirred in 150 mL of dry THF under N2 at 0° C. (ice bath). At total of 3.39 g (15.7 mmol) of dimethylvinylsulfonium iodide was added after 20 minutes, and then the reaction mixture was stirred overnight (about 15 hours). A total of 3.38 g of NaN3 (50 mmol) in 20 mL of 1:1 acetone:water was added to the reaction mixture, and then the reaction mixture was stirred at room temperature for about 12 hours. The mixture was evaporated under reduced pressure, and then purified by flash chromatography (3:2 petroleum ether:ethyl acetate). A yellow oil (2.0 g) was obtained (72%). 1H NMR (CDCl3): δ2.42 (d, 1H, J=5.5), 3.96 (dd, 1H, J=2.5, J2 =11), 4.39 (dd, 1H, J1 =5.5, J2 =11), 4.76 (m, 1H), 4.84 (br s, 1H), 6.56 (s, 1H), 7.10-7.39 (m, 3H), 7.65 (d, 1H, J=7.5). 13C NMR (CDCl3 (CDCl3): δ50.2, 64.6, 79.8, 96.4, 109.7, 119.8, 121.5, 122.1, 131.9, 132.9, 137.1.

Provenance & Evidence