2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 57668735, compound

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Reaction Steps

Into a solution of 3 (4.2 g, 13.9 mmol) in THF (80 ml) was added BuLi (2.5 M in hexane, 6.95 ml, 17.4 mmol) dropwise at −78° C. The mixture was stirred at this temperature for 3 hours before 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (4.05 g, 21.75 mmol) was added in one portion. The reaction mixture was allowed to warm up to room temperature over a period of 12 hours, quenched with water, and then extracted with ether. The organic extracts were combined, washed with brine and water, and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by column chromatography on silica gel with hexane/methylene chloride 3:1 (v/v) as the eluent to yield 4 (3.95 g, 81%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 8.60 (s, 1H), 8.15-8.10 (d, 1H), 7.90-7.85 (d, 1H), 7.45-7.35 (m, 3H), 7.25-7.15 (m, 1H), 4.10-4.09 (d, 2H), 2.42-2.30 (m, 1H), 1.39 (s, 12H), 0.97-0.95 (d, 6H).

Provenance & Evidence