Triphenylphosphine → 2-(3,6-dihydro-2H-pyran-4-yl)-4-nitro-pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7.00 g (44.2 mmol) 2-chloro-4-nitropyridine in 150 ml N,N-dimethylformamide were added 16.8 g (45.0 mmol) tributyl-(3,6-dihydro-2H-pyran-4-yl)stannane, 3.72 g (5.30 mmol) bis(triphenylphosphine)palladium(II) chloride, 6.95 g (26.5 mmol) triphenylphosphine, 15.0 g (353 mmol) lithium chloride and 0.97 g (4.42 mmol) 2,6-di-tert-butyl-p-cresol. The mixture was heated at 100° C. for 4 h and then cooled to room temperature and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 9/1 then ethyl acetate) afforded 2.10 g (23%) 2-(3,6-dihydro-2H-pyran-4-yl)-4-nitro-pyridine as an orange solid. ES-MS m/e (%): 207 (M+H+, 100).

Provenance & Evidence