Sodium Carbonate → HCID 59812138, compound

Participants

Reaction Steps

A mixture of 3 (300 mg, 0.596 mmol), EtOH (3.6 mL), toluene (3.6 mL), furan-3-boronic acid (100 mg, 0.894 mmol), 1M aq. Na2CO3 (1.49 mL, 1.49 mmol), LiCl (75.8 mg, 1.79 mmol) and PdCl2(PPh3)2 (41.8 mg, 59.6 μmol) was refluxed for 15 min. The organic layer was separated, brine was added, and the aqueous layer was extracted with AcOEt. The combined organic solutions were concentrated and separated by means of silicagel chromatography using hexane:AcOEt as eluent (in gradient up to 15% AcOEt) to give 4 as an orange foam (205 mg, 78%); 1H NMR (400 MHz, CDCl3) δ 3.03 (s, 6H), 6.73 (m, 1H), 6.84 (d, J=8.8 Hz, 2H), 7.45-7.65 (m, 6H), 7.84 (s, 2H), 8.05 (d, J=2.1 Hz, 1H), 8.26 (m, 2H), 8.68 (d, J=2.2 Hz, 1H).

Provenance & Evidence