Allyl bromide → HCID 124009256, compound

Participants

Reaction Steps

A 20 ml vial was charged with 22 (33.3 mg, 0.08 mmol) and Cs2CO3 (39.3 mg, 0.12 mmol) and to which was added 1 ml of dry acetone, followed by allyl bromide (19.4 mg, 0.16 mmol). The resulting mixture was stirred at room temperature for 16 h and the solid was filtered of, washed with acetone. The solvent was evaporated and the crude residue was purified by flash column chromatography on silica gel (4 g column, EtOAc/heptane: 0>>>100%) to afford 17.5 mg (43.1%) of 24 as a white solid. 1H NMR (CD3OD) δ 7.71 (d, J=8.08 Hz, 1H), 7.60 (d, J=7.58 Hz, 1H), 7.13-7.28 (m, 3H), 6.87 (s, 1H), 6.14 (m, 1H), 5.47 (dd, J=17.18, 2.02 Hz, 1H), 5.24 (dd, J=10.61, 1.52 Hz, 1H), 4.51 (d, J=9.60 Hz, 1H), 4.47 (dd, J=12.63, 5.05 Hz, 1H), 4.35 (dd, J=12.63, 5.05 Hz, 1H), 4.23 (s, 2H), 3.47-3.73 (5H), 2.23 (s, 3H), 2.20 (s, 3H), 2.01 (m, 1H), 1.48 (q, J=11.12 Hz, 1H). MS (ES) 477.1 (M+Na+).

Provenance & Evidence