Tetrahydrofuran → 7,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-oxa-chrysen-2-ol
Reaktionsgleichung
[OH:1][CH:2]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31]N2CCCCC2)=[CH:25][CH:24]=1)[C:3]1[C:12]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=2F)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([OH:22])=[CH:8]2.C[C:39]([O-])([CH3:41])[CH3:40].[K+].[Cl-].[NH4+:45].[CH2:46]1COC[CH2:47]1>>[F:20][C:15]1[CH:16]=[C:17]([F:19])[CH:18]=[C:13]2[C:14]=1[O:1][CH:2]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:45]3[CH2:41][CH2:39][CH2:40][CH2:47][CH2:46]3)=[CH:27][CH:28]=1)[C:3]1[C:12]2=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([OH:22])=[CH:8]2Komponenten
5
Edukt 4
Produkt 1
Versuchsvorschrift
Dissolve 5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-6-(2,3,5-trifluoro-phenyl)-naphthalen-2-ol (4.3 g, 3.0 mmol) in dry THF (85 mL). Add KOtBu (2.4 g, 21.3 mmol) and stir at room temperature for 3 hours. Pour into saturated aqueous ammonium chloride and extract twice with methylene chloride. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo to yield 3.7 g (90%) of the title compound: mass spectrum (ion spray) m/z=488.2 (M+H). The mixture is purified by chiral chromatography (conditions P). The two isomers eluted with retention times of 6.9 and 8.6 minutes.
Aufarbeitung
- extractionextract twice with methylene chloride
- dry with materialDry the organic layer with sodium sulfate
- filtrationfilter
- concentrationconcentrate in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-d9546a1889b84eae819866f34a05caf0
- Quelldatensatz
- uspto-grants-2012_07
- Patentnummer
- US08217032B2
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