Reaction equation
C([Li])CCC.CCOCC.[CH:11](=[C:15]1[C:23]2[CH:22]=[CH:21][O:20][C:19]=2[CH2:18][CH2:17][CH2:16]1)[CH2:12][CH2:13][CH3:14].[C:24](=[O:26])=[O:25]>C(Cl)(Cl)(Cl)Cl>[CH:11](=[C:15]1[C:23]2[CH:22]=[C:21]([C:24]([OH:26])=[O:25])[O:20][C:19]=2[CH2:18][CH2:17][CH2:16]1)[CH2:12][CH2:13][CH3:14]Participants
Procedure
To a mixture of 1.66 N n-butyl lithium (nBuLi) (328 m 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 organic 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.
Workup
- additionwas added
- 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 organic layer was washed with brine
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-9a30b421d6bc4437990d8b09019244d3
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093710
Linked notes
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