[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23](OC)=[O:24].[Cl-].[NH4+]>O1CCCC1>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:23](=[O:24])[CH2:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:27]=[CH:28][CH:29]=1
To a solution of 4-methyl-pyridine (1.04 mL, 10.74 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. a 1 M solution of sodium hexamethyldisilazide in tetrahydrofuran (21.5 mL, 21.5 mmol, 2 eq) was added dropwise and the reaction was stirred for 20 minutes. Neat methyl 3-methoxybenzoate (1.8 g, 10.74 mmol, 1 eq) was then added and the reaction was stirred at 0° C. for one hour. The reaction was poured into saturated ammonium chloride solution and, after basification with saturated aqueous NaHCO3, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was taken up with n-hexane and filtered to give 1.75 g (72%) of the desired product as beige solid (1.775 g, 50%).
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