Reaktionsgleichung
[Mg].[Cl:2][C:3]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:4]=1[O:10][CH3:11].[Si](O[CH:20]1[CH2:24][C:23](=[O:25])[C:22]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=2)=[CH:21]1)(C(C)(C)C)(C)C.[O:38]1CCCC1>>[OH:38][CH:24]1[C:23](=[O:25])[C:22]([C:26]2[CH:27]=[C:28]([O:36][CH3:37])[C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=2)=[C:21]([C:7]2[CH:6]=[CH:5][C:4]([O:10][CH3:11])=[C:3]([Cl:2])[CH:8]=2)[CH2:20]1Komponenten
5
Versuchsvorschrift
A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3×35 ml), washed with water (2×20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A)
Aufarbeitung
- customReaction
- customwas then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran
- customwas removed under reduced pressure
- customthe residual reaction mixture
- extractionwas extracted with ethyl acetate (3×35 ml)
- washwashed with water (2×20 ml)
- dry with materialdried over sodium sulfate
- concentrationConcentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether)
Quellen und Nachweise
- ORD-Eintrag
- ord-a9576572c5124dd0afedcff1b018c3f3
- Quelldatensatz
- uspto-grants-2007_02
- Patentnummer
- US07179937B2
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