C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C[Mg]Br.[C:12]1(C)C=CC=CC=1.C1COCC1.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C1COCC1>[CH3:12][CH:7]1[CH2:8][C:3](=[O:2])[CH:4]=[CH:5][N:6]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]
4-methoxypyridine (796 g, 7.29 mole) was stirred in 8 L of anhydrous THF in a 20 L reactor. The reactor was cooled to −30° C., then methylmagnesium bromide (5.1 L, 7.29 mole) was added as a 1.4M solution in 3:1 toluene/THF was added via cannula one 800 mL bottle at a time with 800 mls added over a 5 min time period. After the addition was complete and the reaction temperature was −30° C., benzyl chloroformate (1244 g, 7.29 mole) was added dropwise over a 60 min period via addition funnel. The warmest temperature reached was 16° C. After addition was complete the reaction was warmed to 25° C. and stirred for 1.5 hrs. The reaction was cooled to 0° C. and quenched with 4.0 L of 2 N HCl. 4 L of MTBE and brine was added and the layers separated. The temperature was now 25° C. The aqueous phase was extracted with 2×2 L of MTBE. The combined organics were washed with brine and dried over Na2SO4, filtered and concentrated to give the crude oil. Chromatography using a Varian Metaflash 150 long (15 cm×60 cm long 5 kilo silica) and eluting with 10-35% EtOAc/Heptanes gave the product as an oil.
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