Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH:9]=[CH:10][O:11][CH3:12])[CH:3]=1.C([Mg]Cl)(C)C.C([Li])CCC.[CH:23](N1CCOCC1)=[O:24].[Cl-].[NH4+]>CC1CCCO1.C1COCC1.CCCCCC>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:23]=[O:24])=[CH:3][C:4]=1[CH:9]=[CH:10][O:11][CH3:12]4-Bromo-1-fluoro-2-(2-methoxyvinyl)benzene (limiting reagent) (step c) was dissolved in 2-methyltetrahydrofuran (5 volumes) and the solution cooled to −10° C. Iso-propylmagnesium chloride (0.37 molar equivalents of a 2M solution in THF) was added dropwise, keeping the temperature at −7° C. (+ or −2° C.), over about 30 minutes, followed by Butyllithium (0.74 molar equivalents of a 1.5M solution in hexane), controlling the temperature at −6° C. (+ or −2° C.), over about 1 hour. Stirred for 45 minutes then added to a solution of 4-formylmorpholine (2 molar equivalents) in 2-methyltetrahydrofuran (7 volumes) at −5° C. This addition took about 90 minutes. The reaction was then stirred for 1 hour, during which time the internal temperature rose to 5° C. The reaction mixture was poured into saturated aq. ammonium chloride solution (10 volumes) and extracted with t-BME (2×3 volumes). Combined extracts were washed with sat'd aq. ammonium chloride (until the pH of the washing was approx 6) (2×3 volumes), water (5 volumes), dried (Na2SO4), filtered and evaporated to give a mobile orange oil.
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