C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[N:6]=1)=[O:4].O.[OH-].[Li+]>CO.C(OCC)(=O)C>[Cl:22][C:18]1[CH:17]=[C:16]([C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=2[CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)[CH:21]=[CH:20][CH:19]=1A mixture of 6-(3-chlorophenyl)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester (0.3 g, 1 mmol) and lithium hydroxide monohydrate (CAN 1310-66-3, 130 mg, 3 mmol) in THF/H2O 1/1 (20 mL) was stirred at room temperature for 1 h. After removal of the organic solvent under reduced pressure the aqueous phase was washed with ethyl acetate (10 mL) and acidified with 1 N HCl to pH=3. The resulting solution was extracted with ethyl acetate (2×20 mL). The organic layer was concentrated under reduced pressure to give the title compound (0.28 g, 98%) as black oil which was used in the next step without further purification; MS (EI): m/e=304.0 [M+H]+.
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