Water → 1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanone
Reaktionsgleichung
Br[C@@:2]1([C:14](=[O:16])[CH3:15])[C@:10]2([CH3:11])[C@H:5](/[C:6](=[CH:12]/[Br:13])/[CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1.[Br-].[Li+].C(=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O>[Br:13]/[CH:12]=[C:6]1\[CH2:7][CH2:8][CH2:9][C@@:10]2([CH3:11])[C@H:5]\1[CH2:4][CH:3]=[C:2]2[C:14](=[O:16])[CH3:15]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
1-{(E,1R,3aS,7aS)-1-bromo-4-(bromomethylene)-octahydro-7a-methyl-1H-indene-1-yl}ethanone (Compound 12: 100 mg, 0.369 mmol) was dissolved in dimethylformamide (1.6 ml), and lithium bromide (35.8 mg, 0.412 mmol) and lithium carbonate (27.4 mg, 0.371 mmol) were added thereto. The resulting mixture was heated to 100° C. and stirred for 3 hours. After cooling the reaction solution to room temperature, water was added thereto, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over sodium sulfate, and evaporated to obtain a crude product. The product was purified by flash column chromatography to obtain 1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanone (71.6 mg, 94.0%) as a white solid.
Aufarbeitung
- temperatureAfter cooling the reaction solution to room temperature
- extractionthe resulting mixture was extracted with diethyl ether
- washThe organic layer was washed with saturated brine
- dry with materialdried over sodium sulfate
- customevaporated
- customto obtain a crude product
- customThe product was purified by flash column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-c008845b63ed4517b566228e26c40fb7
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08173824B2
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