Phosphine → HCID 178450836, compound

Participants

Reaction Steps

A mixture of compound 94C (2.97 g, 4.27 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.35 g, 0.854 mmol) and palladium acetate (0.096 g, 0.427 mmol) in THF (20 mL) was stirred at room temperature for 5 min. To this solution was added 0.5 M (2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide (17.08 mL, 8.54 mmol) dropwise at room temperature. The reaction was stirred overnight. To the solution were added 2′,6′-dimethoxybiphenyl-2-yl)phosphine (170 mg), palladium acetate (42 mg) and (2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide (15 mL). The resulting mixture was stirred for another 6 hours and concentrated. The residue was loaded on a silica gel column and eluted with 7:3/hexanes:EtOAc to afford 2.75 g of desired product 94D which is a mixture of two isomers. APCI (+) LC/MS: 717 (M+H)+.

Provenance & Evidence