[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14]#[CH:18])=[CH:4][CH:3]=1
A mixture of 5-[(4-chlorobenzyl)oxy]-1-methyl-1H-pyrazol-4-carbaldehyde (125 mg), potassium carbonate (173 mg), dimethyl (1-diazo-2-oxopropyl)phosphonate (192 mg) and methanol (2.5 mL) was stirred at a room temperature for 24 hours. Thereafter, a saturated sodium hydrogencarbonate aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 70:30), so as to obtain the title compound (76 mg) in the form of a light yellow oily substance.
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