Reaktionsgleichung
CO[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([OH:13])=[CH:10]2)=[CH:5][CH:4]=1>C1C2C(=CC=CC=2)C=CC=1O.C(Cl)(Cl)(Cl)Cl>[CH:4]1[CH:5]=[C:6]2[CH:7]=[CH:8][C:9]([OH:13])=[C:10]([C:10]3[C:11]4[C:6](=[CH:5][CH:4]=[CH:3][CH:12]=4)[CH:7]=[CH:8][C:9]=3[OH:13])[C:11]2=[CH:12][CH:3]=1Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
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-methoxy-2-naphthol (35 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 3b, Yield 95%. [α]D25=−104.7 (c=0.35 in EtOAc), 1HNMR (300 MHz, CDCl3) δ (ppm) 7.88 (d, J=9.0 Hz, 2H, 2×HC (5)), 7.79 (d, J=9.0 Hz, 2H, 2×HC (4)), 7.22 (d, J=8.7 Hz, 2H, 2×HC (3)), 7.03 (dd, J=9.0 Hz, 2.4 Hz, 2H, 2×HC (6)), 6.49 (d, J=2.4 Hz, 2H, 2×HC (8)), 5.08 (s, 2H, 2×OH), 3.59 (s, 6H, 2×OCH3). e.e. 95%, and the configuration was R (Kromasil CHI-TBB column, Hexane/propan-2-ol=80: 20; flow rate 1 mL/min; S-isomer, tR 4.95 min and R-isomer, tR 5.32 min).
Aufarbeitung
- customA reaction flask described in example 9
- stirringThe reaction mixture was stirred at 0° C. until the reaction
- concentrationThe crude mixture was concentrated under reduced pressure
- custompurified by column chromatography (Ethyl acetate/Petroleum ether=⅓)
Quellen und Nachweise
- ORD-Eintrag
- ord-a53c68accfa741cc84bff95150ef01ff
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07151070B2
Verknüpfte Notizen
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