Potassium Carbonate → HCID 69627441, compound

Participants

Reaction Steps

To a stirred solution of 3,3″-dichloro-5′-[6-(naphthalen-1-ylcarbamoyloxy)-hexylcarbamoyl]-[1,1′;3′1″]-terphenyl-2′-ol (0.320 g, 0.510 mmol) and K2CO3 (0.078 g, 0.561 mmol) in DMF (10 mL) at room temperature was added dropwise methyl bromoacetate (0.097 mL, 1.02 mmol). After 18 h at this temperature, it was concentrated and then diluted with excess EtOAc (250 mL). The organic layer was washed with 1 N HCl (25 mL), sat. aq. NaHCO3 (25 mL), and brine (25 mL) and then dried (MgSO4). After concentration, the residue was purified by flash chromatography (30 to 50% EtOAc/petroleum ether gradient) to afford the product (0.231 g, 65%) as a solid; 1H NMR (DMSO-d6) δ1.32-1.49 (m, 4H), 1.49-1.73 (m, 4H), 3.23-3.35 (m, 2H), 3.44 (s, 3H), 3.99 (s, 2H), 4.11 (t, J=6.3 Hz, 2H), 7.45-7.63 (m, 10H), 7.69 (s, 2H), 7.73 (d, J=9.4 Hz, 1H), 7.87-7.94 (m, 3H), 8.02-8.12 (m, 1H), 8.61 (t, J=5.5 Hz, 1H), 9.49 (s, 1H); mass spectrum [(+) ESI], m/z 700 (M+H)+.

Provenance & Evidence