Triisopropyl borate → HCID 86710788, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-bromo-2-(but-3-en-1-yl)pyridine (Ref. Zhang, Z; Dwoskin, L. and Crooks, P. Tetrahedron Lett. 2011, 52, 2667-2669, 550 mg, 2.59 mmol) and triisopropyl borate (0.775 mL, 3.37 mmol) in toluene (4 mL) and THF (1 mL) cooled to −78° C. was added 2.5 M n-BuLi (1.349 mL, 3.37 mmol) over the course of 15 min. During this time period, the reaction color changed from yellow to orange. The reaction was stirred at −78° C. for 2 h then warmed to 0° C. for 15 min. It was then quenched with 2 N HCl (5 mL) and stirred for 10 min. The solution became a slurry (pH was found to be 3). It was then diluted with ether, the ether layer was discared. The aqueous layer was adjusted pH=7-8. A white cloud was formed. It was then extracted with EtOAc, the organic layer was dried over MgSO4, filtered and concentrated to obtain 450 mg (98%) of the desired product as a white foam. LCMS (M+1)=178.1.

Provenance & Evidence