4-Chlorophenylboronic acid → 2-(4-Chloro-benzyl)-tetrahydropyran

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of (4-chlorophenyl)dihydroxyborane (524.0 mg, 3.351 mmol), 2-aminocyclohexanol hydrochloride (42 mg, 0.28 mmol) and nickel iodide (87.3 mg, 0.279 mmol) in i-PrOH (10.00 mL) was added sodium hexamethyldisilazane (1.075 g, 5.864 mmol) at 0° C. Then the mixture was stirred at rt for 5 min before, 2-(bromomethyl)tetrahydro-2-H-pyran (500.00 mg, 2.79 mmol) was added by syringe. The resulting mixture was then stirred at 60° C. for 5 h. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography(5% AcOEt in hexane). 1H NMR (400 MHz, MeOD) δ 1.20-1.34 (m, 1H), 1.43-1.62 (m, 4H), 1.75-1.85 (m, 1H), 2.61-2.80 (m, 2H), 3.36-3.54 (m, 2H), 3.85-3.95 (m, 1H), 7.12-7.32 (m, 4H).

Provenance & Evidence