Triisopropyl borate → HCID 59224667, compound

Participants

Reaction Conditions

Reaction Steps

The crude product containing 4-benzyloxy-2-iodo-1-methybenzene (32.9 g, 101.5 mmol) obtained in Step 1 above and triisopropyl borate (28.1 ml, 121.8 mmol) were placed in a reaction vessel, and then tetrahydrofuran (43 ml) and toluene (170 ml) were added thereto. The resulting mixture was cooled to −78° C., and n-butyllithium (1.6N; n-hexane solution, 76.2 ml, 121.9 mmol) was added dropwise thereto over 30 minutes. The resulting reaction solution was stirred at −78° C. for 30 minutes. After the solution was warmed to 0° C., neopentylglycol (12.7 g, 121.9 mmol) was added thereto and stirred at room temperature for 16 hours. The reaction solution was diluted with dichloromethane (1200 ml), and sequentially washed with a saturated aqueous ammonium chloride solution (1200 ml) and water (1200 ml). The solution was then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to yield 2-(5-benzyloxy-2-methylphenyl)-5,5-dimethyl-[1,3,2]dioxaborinane (41.5 g) as a crude product.

Provenance & Evidence