[Cl:1][C:2]1[CH:3]=[CH:4][C:5](C)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.[C:24]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:25]C([O-])=O.[K+].[Cl-].[Mg+2].[Cl-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:17])=[C:6]([C:7](=[O:9])[CH2:25][C:24]([O:30][CH2:31][CH3:32])=[O:29])[CH:10]=1To a stirring solution of 5-chloro-2-methylbenzoic acid (4.85 g, 28.4 mmol) in tetrahydrofuran (30 mL) was added N,N-carbonyldiimidazole (4.87 g, 30.0 mmol, 1.06 equiv). After 30 minutes, the reaction mixture was added to a suspension of potassium ethyl malonate (11.61 g, 68.22 mmol, 2.40 equiv) and magnesium chloride (3.27 g, 34.3 mmol, 1.21 equiv) in tetrahydrofuran (50 mL). The resultant suspension was heated at 50° C. After hours, the reaction mixture was partitioned between ethyl acetate and water. The organic portion was dried over magnesium sulfate, filtered, and concentrated to provide 8.07 g (118%) of ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate which was used without purification. LCMS (ESI) m+H=241.2
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