Propargyl bromide → HCID 25178773, compound

Participants

Reaction Steps

To a stirred solution of 18 (0.40 g, 2 mmol) in dry DMF (10 mL) was added potassium hydroxide (0.56 g, 10 mmol), followed by dropwise addition of propargyl bromide (80 wt. % in toluene) (0.48 g, 4 mmol) over 5 min. After 18 h the reaction mixture was poured onto water (30 mL) and washed with DCM (3×15 mL). The combined organic fractions concentrated in vacuo and the liquid remaining taken up in diethyl ether (15 mL) and washed with water (2×10 mL), then brine (1×10 mL) and dried over Na2SO4. Chromatography (hexanes/ethyl acetate) gave the desired product as a colorless oil (0.32 g, 67%). HRMS (ESI)=240.1597 (M+H)+. Calcd. for C13H22NO3 240.1594. 1H NMR (600 MHz, CDCl3) δ 4.13 (s, 2H), 3.96-3.88 (m, 1H), 3.64 (dd, J=9 Hz, J=3.6 Hz, 1H), 3.49-3.22 (m, 3H), 2.40 (s, 1H), 1.94-1.78 (m, 4H), 1.46 (s, 9H). TLC (I2) Rf=0.67 (1:1 hexanes/ethyl acetate).

Provenance & Evidence