7-(2-Propenyloxy)-2-naphthalenol → Binol

Participants

Reaction Steps

A reaction flask described in example 9 was charged with a solution of catalyst 1 c (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-allyloxy-2-naphthol (40 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 3i, Yield 99%. [[α]D25=−186.5 (c=0.4 in EtOAc), 1HNMR (300 MHz, CDCl3) δ (ppm) 7.87 (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, 3.0 Hz, 2H, 2×HC (6)), 6.49 (s, 2H, 2×HC (8)), 5.08 (s, 2H, 2×OH), 3.66–3.78 (m, 4H, 4×OCH2), 1.58–1.67 (m, 4H, 4×OCH2CH2), 1.20–1.40 (m, 4H, 4×CH2CH3), 0.87–0.89 (t, 6H, 6×CH3). e.e. 95%.

Provenance & Evidence