Reaktionsgleichung
C([Li])CCC.[CH:6](=[C:10]1[C:18]2[CH:17]=[CH:16][O:15][C:14]=2[CH2:13][CH2:12][CH2:11]1)[CH2:7][CH2:8][CH3:9].[C:19](=[O:21])=[O:20].C(Cl)(Cl)(Cl)Cl>CCOCC>[CH:6](=[C:10]1[C:18]2[CH:17]=[C:16]([C:19]([OH:21])=[O:20])[O:15][C:14]=2[CH2:13][CH2:12][CH2:11]1)[CH2:7][CH2:8][CH3:9]Komponenten
Versuchsvorschrift
To a mixture of 1.66 N n-butyl lithium (nBuLi) (328 ml in n-hexane solution) and Et2O (100 ml) was added a mixture of 4-n-butylidene-4,5,6,7-tetrahydrobenzo[b]furan (9.60 g) and Et2O (50 ml) dropwise over 5 minutes while maintaining −30˜−20° C. by dry ice—carbon tetrachloride (CCl4) cooling. The reaction mixture was stirred at r.t. for 1 hour, and was bubbled by carbon dioxide (CO2) gas for 1 hour. The whole mixture was stirred at r.t. overnight and poured into a mixture of water and Et2O. The separated aqueous layer was adjusted to pH 1.4 with 10% HCl, and extracted by AcOEt. The orgaic layer was washed with brine, dried over MgSO4, and evaporated to give 4-n-butylidene-4,5,6,7-tetrahydrobenzo[b]furan-2-carboxylic acid (3.91 g) as a reddish oil, which was used in the next reaction without further purification.
Aufarbeitung
- additionwas added
- temperaturecooling
- customwas bubbled by carbon dioxide (CO2) gas for 1 hour
- stirringThe whole mixture was stirred at r.t. overnight
- additionpoured into a mixture of water and Et2O
- extractionextracted by AcOEt
- washThe orgaic layer was washed with brine
- dry with materialdried over MgSO4
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-1da8c24409d24c3f88c79c3824f705e9
- Quelldatensatz
- uspto-grants-2001_08
- Patentnummer
- US06274619B1
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