Sodium hydride → HCID 67286765, compound

Participants

Reaction Conditions

Reaction Steps

step 4—To a solution of 4-nitro-benzyltriphenylphosphonium bromide (829 mg, 1.734 mmol) in DMF (5 mL) at 0° C. was added NaH (60% in oil dispersion, 133 mg, 3.32 mmol). The reaction was stirred for 30 min at 0° C. and followed by addition of a solution of 66 (215 mg, 0.553 mmol) in DMF (5 mL). The resulting mixture was gradually warmed to RT and stirred overnight. The reaction was quenched with 1N aqueous HCl solution (6 mL) then 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 (0 to 4% EtOAc) to afford 180 mg (64%) of 2-benzyloxy-3-{3-tert-butyl-4-methoxy-5-[2-(4-nitro-phenyl)-vinyl]-phenyl}-6-methyl-pyridine (68) as an orange oil.

Provenance & Evidence