Tributylphosphine → HCID 23159944, compound

Participants

Reaction Steps

To a mixture of methyl 4-[(3-tert-butyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)methyl]benzoate (1.68 g, 5.83 mmol), (6-methylpyridin-2-yl)methanol (0.79 g, 6.4 mmol), tributylphosphine (2.90 mL, 11.6 mmol) and tetrahydrofuran (80 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.94 g, 11.7 mol), and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and diisopropyl ether was added to the residue. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:3) to give the title compound (2.14 g, yield 93%) as a yellow oil. 1H NMR (CDCl3) δ: 1.27 (9H, s), 2.54 (3H, s), 3.90 (3H, s), 5.11 (2H, s), 5.25 (2H, s), 5.47 (1H, s), 6.96 (1H, d, J=7.8 Hz), 7.06 (1H, d, J=7.8 Hz), 7.19 (2H, d, J=8.6 Hz), 7.51 (1H, t, J=7.7 Hz), 7.93-8.00 (2H, m).

Provenance & Evidence