[H-].[Na+].[CH:3]([O:5][CH3:6])=[O:4].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=O)=[CH:10][CH:9]=1.CI>O1CCCC1.CO.CN(C)C=O.O>[CH3:18][O:17][CH:15]=[C:14]([C:11]1[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4]
Suspend sodium hydride (3.4 g, 142 mmol) in anhydrous tetrahydrofuran (100 mL). Cool in an ice/water bath. Add methyl formate (8.8 mL, 142 mmol), methanol (1 drop), and methyl 4-fluorophenylacetate. Warm slowly to ambient temperature. After 18 hours, concentrate in vacuo to give a residue. Dissolve the residue in dimethylformamide and cool in an ice/water bath. Add methyl iodide (8.0 mL, 130 mmol). Warm slowly to ambient temperature. After 3.5 hours, pour the reaction mixture into water and extract twice with ether. Dry the combined organic layers over MgSO4 filter, and concentrate in vacuo to give the title compound: Rf =0.52 (silica gel, 2/1 hexane/ethyl acetate).
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