Nitrogen → HCID 59590904, compound

Participants

Reaction Steps

A 200 mL round bottom flask was charged with copper(II) trifluoromethanesulfonate (0.087 g, 0.24 mmol) and DME (12 mL), cooled to −40° C. (dry ice/acetone), and subjected to 3 cycles of evacuation/back-filling with N2. To the cold solution were added diethylzinc (1.0 M solution in hexanes, commercially available from Aldrich) (12 mL, 12 mmol) and a solution of 18.1 (0.694 g, 2.4 mmol) in DME (12 mL) slowly under N2. The mixture was warmed to room temperature and stirred for 2 days. The reaction was carefully quenched with 1 N HCl (15 mL) and diluted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by silica gel flash chromatography (0-30% EtOAc/hexanes) to afford 42.1 (0.31 g, 40% yield) as a yellow oil.

Provenance & Evidence