Propargyl alcohol → HCID 59372952, compound

Participants

Reaction Steps

A solution of propargyl alcohol (46 mg, 0.81 mmol) and KN(TMS)2 (1.63 mL, 0.81 mmol) in tetrahydrofuran (1.5 mL) is stirred under argon for 30 min before 1-bromomethyl-4-chlorophthalazine (2) (140 mg, 0.54 mmol) is added. The mixture is stirred for 3 h, quenched with 2 N HCl (5 mL) and H2O (15 mL), and extracted with ethyl acetate (80 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (20% to 25% ethyl acetate/hexane) to give 29 mg (23%) of 3 as a colorless solid, mp 131-132° C. IR 3079, 1406, 1325 cm−1; 1H NMR (CDCl3) δ 2.60 (t, J=2.4 Hz, 1H, CH≡CCH2O), 5.17 (s, 2H, CH2), 5.36 (d, J=2.4 Hz, CH≡CCH2O), 7.90-8.02 (m, 2H, 6,7-PhthH), 8.21 (m, 1H, 5-PhthH), 8.36 ppm (m, 1H, 8-PhthH).

Provenance & Evidence