Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH3:9].[Li][CH2:11][CH2:12][CH2:13][CH3:14].[O:15]1[C@H](CC)C1>C1COCC1>[CH2:13]([C:12]1[CH:11]=[CH:4][CH:5]=[CH:6][C:7]=1[C@H:2]([OH:15])[CH2:3][CH2:8][CH3:9])[CH3:14]The 1-bromo-2-ethylbenzene (2.0 g) was dissolved in dry THF and the mixture was cooled to −78° C. 1.6 M n-BuLi (20.26 ml) was slowly added to the reaction mixture and then the mixture was stirred at −78° C. After 1 h (R)-(+)-1,2-epoxybutane (1.1 g) was added in 10 ml of THF. The reaction mixture was allowed to warm to ambient temperature and then stirred over night. The reaction was quenched with ice-water and product extracted in heptanes, and finally purified by using the separation method E yielding the title compound (1.1 g).
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