Reaktion #946274

Reaktionsgleichung

7-octyloxy-2-naphthol

→

(R)-BINOL

Ausbeute 99.0%

Lösungsmittel

CCl4

CCl4

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA reaction flask described in example 9
2. 2
   workup.STIRRINGThe reaction mixture was stirred at 0° C. until the reaction
3. 3
   EinengenThe crude mixture was concentrated under reduced pressure
4. 4
   Sonstigepurified by column chromatography (Ethyl acetate/Petroleum ether=⅓)

Vorschrift

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-octyloxy-2-naphthol (54 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 3j, Yield 99%. [α]D25=−153.8 (c=0.5 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, 2.4 Hz, 2H, 2×HC (6)), 6.49 (d, J=2.1 Hz, 2H, 2×HC (8)), 5.07 (s, 2H, 2×OH), 3.67–3.77 (m, 4H, 4×OCH2), 1.59–1.66 (m, 4H, 4×OCH2CH2), 1.25–1.29 (m, 20H, 20×CH2), 0.86–0.90 (t, 6H, 6×CH3). e.e. 94%.

Quelle