[H-].[Na+].C[OH:4].Br[C:6]1[C:7](=O)[O:8][C:9]2C(C=1C)=C[CH:12]=[C:11]([OH:17])[CH:10]=2.CN([CH:22]=[O:23])C>Cl>[CH3:22][O:23][CH2:12][C:11](=[O:17])[CH2:10][C:9]([O:8][CH2:7][CH3:6])=[O:4]
NaH (7.71 g, 192.7 mmol) was suspended in DMF (110 mL). The solution of MeOH (2.64 g, 82.5 mmol) in DMF (55 mL) was added drop wise at 0° C. After that, the mixture was stirred at 0° C. for 30 min. The solution of compound 1 (9.54 g, 57.9 mmol) in DMF (55 mL) was added dropwise at 0° C., then the reaction mixture was allowed to warm slowly to RT and stirred for 16 h. The reaction mixture was diluted with 1N HCl (400 mL), extracted with MTBE (250 mL×3). The combined organic layer was washed with H2O (200 mL×5), dried over Na2SO4, filtered, concentrated, purified by silica gel column (PE:EA=10:1) afforded ethyl 4-methoxy-3-oxobutanoate (1.4 g, 15.1%) as light yellow oil.
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