Potassium Carbonate → HCID 57501699, compound

Participants

Reaction Steps

To an oven-dried round bottom flask, add 2-methoxy-4-nitro-phenol (2.45 g, 14.5 mmol) and purge with nitrogen. Add DMF (25 mL) by syringe, followed by K2CO3 (3.0 g, 21.7 mmol) and KI (catalytic) neat. Stir 30 min at room temperature and add 2-bromo-1,1-dimethoxy-ethane (1.9 mL, 15.9 mmol) by syringe. Attach a reflux condenser and stir overnight in a 120° C. oil bath. Quench with water, extract with ether (3×), dry over MgSO4, filter and concentrate under vacuum. Add xylenes and concentrate again under vacuum. Purify by flash chromatography on silica gel using a gradient of EtOAc/hexane (20% to 60%) to give the title compound as a white residue (2.55 g, 68%). Exact mass=257.1, MS (ES+) 258.2 (M+1)+. 1H NMR (CDCl3): δ 7.88 (dd, J=9.1, 2.8 Hz, 1H), 7.74 (d, J=2.8 Hz, 1H), 6.94 (d, J=9.1 Hz, 1H), 4.77 (t, J=5.2 Hz, 1H), 4.13 (d, J=4.9 Hz, 2H), 3.93 (s, 3H), 3.48 (s, 6H).

Provenance & Evidence