Tetrahydrofuran → HCID 68887960, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of zinc chloride (0.367 g, 2.7 mmol, 3 eq) and magnesium (0.100 g, 4.1 mmol, 4.7 eq) in tetrahydrofuran (2.5 ml) under argon was added 7 (1.268 g, 3.8 mmol, 4.2 eq) in tetrahydrofuran (2.5 ml). The reaction was heated to 50° C. for 19 hours then cooled. 34 (0.481 g, 0.8 mmol) in tetrahydrofuran (7 ml) and dichlorobis-[tri-(o-tolyl)-phosphinyl]palladium (0.063 g, 0.08 mmol, 0.09 eq) added and the reaction stirred for 25 hours. The reaction was then quenched with 3 N HCl (10 ml), diluted with water and extracted into ethyl acetate (3×). The combined aqueous layers were dried (MgSO4) and concentrated in vacuo to give a purple oil. Column chromatography (silica gel, petrol:EtOAc 9:1>2:1) yielded 48 (0.082 g, 15%) as a pale yellow oil.

Provenance & Evidence