Tributylstannane → HCID 86669799, compound

Participants

Reaction Steps

To a solution of tert-butyl [3-(4-chlorophenyl)prop-2-yn-1-yl]carbamate (5.97 g, 22.5 mmol) in THF (240 mL) under an atmosphere of argon was added bis(triphenylphosphine)palladium(II) chloride (0.788 g, 1.12 mmol) and tri-n-butyltin hydride (9.55 mL, 35.5 mmol). The solution was stirred at room temperature for 90 minutes. The solvent was evaporated and the residue was purified using column chromatography on silica gel (220 g Analogix column, gradient hexane to 20% EA in hexane over 30 minutes) to give the product (11.2 g, 90%). LCMS: (AA) ES+ 556, 558. 1H NMR (400 MHz, d6-DMSO) δ: 7.37-7.31 (m, 2H), 6.96 (m, 2H), 5.83-5.60 (m, 1H), 3.60-3.37 (m, 2H), 1.44-1.36 (m, 6H), 1.34 (m, 9H), 1.26-1.15 (m, 6H), 0.89-0.77 (m, 15H).

Provenance & Evidence