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Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 3.5 h; Stage #2: at 20℃; for 72 h;
PREPARATION 33; 2-(4-phenylboronic acid)propan-2-ol. n-BuLi (2.5 M in hexanes, 1.00 mL, 2.5 mmol) was added to a -78°C solution of PP51 (0.50 g, 2.33 mmol) in THF (20 mL). After 1.5 hrs, an additional 0.95 mL n-BuLi (2.38 mmol) was added and the mixture was stirred for 2 additional hrs. Triisopropyl borate (1.08 mL, 4.66 mmol) was added and the reaction was warmed to rt and stirred for 3 days. 1 N HCI was added and the mixture was extracted 3x with EtOAc. The extracts were washed with brine, dried (MgSO4) and concentrated to give 0.29 g of crude product. Chromatography, first flushing with 50percent EtOAc/ hexanes and then eluting with 10percent MeOH/EtOAc, gave partially EPO <DP n="77"/>pure material which was then triturated with ether to yield 51 mg (13percent) of PP33 as a white solid: NMR (MeOH-d4) 7.67 (d, J = 8.3 Hz, 1 H), 7.54 (d, J = 7.88 Hz, 1 H), 7.45-7.40 (m, 2H), 1.97 (s, 6H).
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