HCID 13938999, compound → Binol

Participants

Reaction Steps

A reaction flask described in example 9 was charged with a solution of catalyst 1c (12.2 mg, 0.02 mmol) in anhydrous CCl4 (1 mL). The solution was stirred for 10 min under an oxygen atmosphere and then treated with a solution of 7-dodecyloxy-2-naphthol (66 mg, 0.2 mmol) in anhydrous CCl4 (1 mL) under 0° C. The reaction mixture was stirred at 0° C. until the reaction was complete (monitored by TLC). The crude mixture was concentrated under reduced pressure, and purified by column chromatography (Ethyl acetate/Petroleum ether=⅓) to give (R)-BINOL 3k, Yield 94%. [α]D25=−86.3 (c=0.2 in EtOAc), 1HNMR (300 MHz, CDCl3) δ (ppm) 7.86 (d, J=9.0 Hz, 2H, 2×HC (5)), 7.78 (d, J=9.0 Hz, 2H, 2×HC (4)), 7.21 (d, J=9.0 Hz, 2H, 2×HC (3)), 7.03 (dd, J=9.0 Hz, 2.1 Hz, 2H, 2×HC (6)), 6.49 (d, J=2.1 Hz, 2H, 2×HC (8)), 5.08 (s, 2H, 2×OH), 3.65–3.79 (m, 4H, 4×OCH2), 1.59–1.67 (m, 4H, 4×OCH2CH2), 1.25–1.27 (m, 36H, 36 ×CH2), 0.88–0.92 (t, 6H, 6×CH3). e.e. 97%.

Provenance & Evidence