Sodium Carbonate → HCID 68703381, compound

Participants

Reaction Steps

A solution of product 5 (1.2 g, 6.1 mmol, 0.08M) in DMSO (75.5 ml) is heated at 175° C. for 1 h 30. After cooling at ambient temperature, the reaction mixture is poured onto water (200 ml), basified (5% Na2CO3) to a pH of greater than 10 and then extracted with DCM (4×150 ml). The aqueous phase is then saturated with NaCl and then extracted with DCM (4×150 ml). The organic phases are combined, dried (MgSO4) and then evaporated. The crude product obtained (6.6 g) is then purified by chromatography on silica gel (DCM (sat. NH3) and then DCM (sat. NH3)/MeOH, 98/2). Product 18 (Rf=0.36, DCM/MeOH(NH3): 98/2) is obtained in the form of a brown semisolid (265 mg, 22%), an inseparable mixture of Z/E (14:86) isomers.

Provenance & Evidence