[H-].[Na+].Br[CH2:4][CH2:5][O:6][CH2:7][CH2:8]Br.[C:10]1([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN1C(=O)CCC1>[C:10]1([C:16]2([C:17]([O:19][CH3:20])=[O:18])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1To NaH (60% dispersion in mineral oil (14.2 g, 355 mmol)) was added NMP (142 mL), and the mixture was cooled to 0° C. A solution of 1-bromo-2-(2-bromoethoxy)ethane (17.8 mL, 142 mmol) and methyl phenylacetate (20.00 mL, 142 mmol) in NMP was added dropwise, and the resulting reaction mixture was stirred at 0° C. for 2 hours. The reaction was quenched with water, acidified to pH=2 with concentrated HCl, extracted with 200 mL of diethyl ether, washed 2 times with 100 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound after flash chromatography (15.40 g) as a white solid. MS m/e=221 (M+H)+.
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