Reaktionsgleichung
[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][CH:9]([OH:12])[C:8]2[CH:7]=[C:6]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:17]=[CH:16]4)[CH:5]=[CH:4][C:3]1=2.C[N+]1([O-])CCOCC1.C(OCC)(=O)C>C(Cl)Cl.O.CCCCCC>[CH2:26]([O:25][C:23]([C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:6]3[CH:5]=[CH:4][C:3]4[C:2]([CH3:28])([CH3:1])[CH2:11][CH2:10][C:9](=[O:12])[C:8]=4[CH:7]=3)[CH:14]=2)[CH:19]=1)=[O:24])[CH3:27]Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
To a solution of 101 mg (0.27 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-7-yl]naphth-2oate (Compound B4) in 1.5 mL of methylene chloride was added 50 mg (0.43 mmol) of N-methylmorpholine N-oxide and 6.0 mg (0.017 mmol) of tetrapropylammonium perruthenate(VII). The reaction was stirred at room temperature for 3 h, diluted with water, and extracted with CH2Cl2 (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give a foam. The title compound was obtained as a white solid after flash chromatography (silica, 10% ethyl acetate in hexane).
Aufarbeitung
- extractionextracted with CH2Cl2 (2×)
- washThe combined organic layer was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customto give a foam
Quellen und Nachweise
- ORD-Eintrag
- ord-594e910d1c0142e197d50a14193f26dd
- Quelldatensatz
- uspto-grants-2005_02
- Patentnummer
- US06855832B2
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