Iodoethane → HCID 66562536, compound

Participants

Reaction Steps

To a solution of compound 1 (500 mg, 1.10 mmol) in dry THF (20 mL) was added LiHMDS (1.0 mL, 1.0 mmol) at −10° C. under N2. After stirring for 30 min, iodoethane (312 mg, 2.0 mmol) was added. The solution was stirred for another 3 h at 35° C., then quenched with water and extracted with EA twice. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered, concentrated and purified by CC (EA/PE=1/5) to give compound 2 (50 mg, 10%) as a solid. 1H-NMR (400 MHz, CDCl3) δ: 0.63-0.65 (m, 2H), 0.97-1.03 (m, 3H), 1.13-1.17 (m, 3H), 1.34 (s, 18H), 1.32-1.35 (m, 3H), 1.50-1.55 (m, 3H), 2.52 (s, 3H), 3.04-3.07 (m, 2H), 3.72 (d, J=6.8 Hz, 2H), 4.12 (m, 1H), 6.41 (s, 1H), 7.15 (s, 2H), 7.40 (s, 1H). MS Calcd.: 472; MS Found: 473 (M+1).

Provenance & Evidence