Sodium Carbonate → HCID 178502091, compound

Participants

Reaction Steps

Compound 6 (0.070 g, 0.32 mmol) is heated in DMSO (5 ml) at 175° C. for 2 h. After cooling to ambient temperature, the reaction mixture is poured onto ice-cold water (100 ml), basified (5% Na2CO3) to a pH of greater than 10 and then extracted with DCM (3×150 ml). The organic phases are combined, washed with saturated NaCl solution, dried (MgSO4) and then evaporated to dryness. The crude product obtained (0.06 g) is then purified by chromatography on thick layers of silica gel (DCM, sat. NH3/MeOH, 95:5). The product (Rf=0.49, DCM/MeOH/NH3 vap., 95:5) is obtained in the form of a brown semisolid (20 mg, 0.09 mmol, 28%), an inseparable mixture of E/Z (9:1) isomers according to 1H NMR.

Provenance & Evidence