2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 131727681, compound

Participants

Reaction Conditions

Reaction Steps

A THF solution (2 mL) of the 4-(diallylethoxysilyl)iodobenzene (171 mg, 0.48 mmol) obtained in Example 2 was added dropwise with 2 mol/L of i-PrMgCl (0.50 mL (solvent: THF), 1.0 mmol) at −30° C. Then, the resultant solution was stirred under a nitrogen atmosphere at −30° C. for 1.5 hours to obtain a THF solution containing 4-(diallylethoxysilyl)phenylmagnesium chloride (Grignrad solution). Subsequently, the obtained Grignrad solution was cooled to −78° C., and added dropwise with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (204 μL, 1.0 mmol) to obtain a reaction mixture. Thereafter, the obtained reaction mixture was stirred under a nitrogen atmosphere at −78° C. for one hour, and further stirred at room temperature for 14 hours. After that, the reaction mixture was added with distilled water to terminate the reaction, and 10% by mass of an HCl solution was further added thereto until the salt thus formed disappeared. Then, the organic layer was separated therefrom, and the aqueous layer was extracted with ether to collect the organic layer. Subsequently, the organic layer thus collected was washed with sat.NaHCO3 and sat.NaCl, dried with MgSO4, filtered, and concentrated to obtain a crude product. Thereafter, the crude product thus obtained was separated and purified by silica gel column chromatography (hexane/EtOAc=5/1), and thereby 1-(diallylethoxysilyl)-4-(4,4,5,5-tetramethyl-1,3,2-di oxaborolan-2-yl)benzene was obtained (128.3 mg, 75% yield).

Provenance & Evidence