Sodium hydride → HCID 67069886, compound

Participants

Reaction Conditions

Reaction Steps

step 3—To a solution of 4-nitro-benzyltriphenylphosphonium bromide (1.07 g, 2.238 mmol) in DMF (8 mL) at 0° C., was added NaH (60% in oil dispersion, 156 mg, 3.90 mmol). The reaction was stirred for 30 min at 0° C. then a solution of 50 (281 mg, 0.749 mmol) in DMF (6 mL) was added. The resulting mixture was gradually warmed to RT and stirred overnight. The reaction was quenched with 1N aqueous HCl solution (6 mL) and diluted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (5 to 10% EtOAc) to afford 311 mg (84%) of 3-{2-benzyloxy-5-tert-butyl-3-[2-(4-nitro-phenyl)-vinyl]-phenyl}-2-methoxy-pyridine (52) as a yellow oil.

Provenance & Evidence