Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH3:10])[CH:3]=1.C([Li])CCC.CN(C)[CH:18]=[O:19].Cl>O1CCCC1.O1CCOCC1.O>[CH2:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:18]=[O:19])[CH2:9][CH3:10]
To a solution of 1-bromo-3-propylbenzene (16.6 g) in tetrahydrofuran (83 ml) cooled to −78° C. was added dropwise n-butyllithium (2.66M solution in n-hexane, 34 ml) over 9 minutes, and then the mixture was stirred for 1 hour. To this reaction solution was added dropwise N,N-dimethylformamide (7.7 ml) over 6 minutes, and the mixture was stirred for additional 20 minutes. To this reaction solution was added dropwise a 4M solution of hydrogen chloride in 1,4-dioxane (23 ml) over 5 minutes, and then the mixture was stirred after warming to room temperature. To this mixed solution was added water (83 ml), followed by a 6M aqueous solution of hydrochloric acid (12 ml), and then the mixture was extracted with n-hexane (80 ml). The resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product of the titled compound (14.0 g).
Wird geladen…
