C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH2:20][CH2:19][CH2:18]2.Br[CH2:27][C:28]([O:30]CC)=[O:29]>C1COCC1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH:20]([CH2:27][C:28]([OH:30])=[O:29])[CH2:19][CH2:18]2
n-Butyl lithium (3.27 g, 51.04 mmol) was added to a solution of di-isopropyl amine (6.88 g, 68.11 mmol) in THF (50 mL) at −60° C., and the mixture was stirred for 0.5 h. 6-methoxy-1-tetralone (6 g, 34.09 mmol) in THF (10 mL) was slowly added to the reaction mixture, the mixture was stirred for 45 min and ethyl bromoacetate (11.9 g, 71.25 mmol) was added. The reaction mixture was then stirred at room temperature for 16 h and quenched with saturated NH4Cl solution. The reaction mixture was extracted with EtOAc (X2), combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentration to give 5.3 g of the title compound.
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