[Li]CCCC.[CH3:6][C:7]1[N:12]=[C:11]([Cl:13])[CH:10]=[CH:9][CH:8]=1.[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17].[NH4+].[Cl-]>C1COCC1.O>[Cl:13][C:11]1[N:12]=[C:7]([CH2:6][C:14]([O:15][CH2:16][CH3:17])=[O:18])[CH:8]=[CH:9][CH:10]=1
To a solution of n-BuLi (100 mL, 250 mmol of a 2.5 M solution in hexanes) in THF (200 mL) was added DIA (36 mL, 255 mmol) at 0° C. After stirring for 45 min, 6-methyl-2-chloropyridine (14.2 g, 111 mmol) was added slowly, maintaining the temperature <5° C. After 30 min, diethyl carbonate (30 mL, 250 mmol) was added dropwise maintaining the temperature below 10° C. The solution was stirred at 0° C. for 1 h, then water was slowly added, followed by the addition of a saturated solution of NH4Cl. The organic phase was dried (Na2SO4), filtered, and then concentrated under reduced pressure. The residue was purified through a pad of silica gel to give the product (13.3 g, 66.6 mmol) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.27 (t, 3H), 2.04 (s, 2H), 4.19 (q, 2H), 7.23 (dd, 2H), 7.62 (t, 1H).
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