C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CO.[CH2:22]([O:29][C:30]1[CH:45]=[CH:44][C:43]([CH:46]=[O:47])=[CH:42][C:31]=1[C:32]([O:34][CH2:35]C1C=CC=CC=1)=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)(=O)C.O>[CH2:22]([O:29][C:30]1[CH:45]=[CH:44][C:43]([C:46]2[O:47][CH:12]=[N:11][CH:10]=2)=[CH:42][C:31]=1[C:32]([O:34][CH3:35])=[O:33])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1p-Toluenesulfonylmethyl isocyanide (0.55 g) and potassium carbonate (0.39 g) were added to a methanol (9 mL) suspension of the obtained benzyl 2-(benzyloxy)-5-formylbenzoate (0.93 g), followed by heating to reflux for 1 hour and 40 minutes. The reaction mixture was cooled to room temperature, and then p-toluenesulfonylmethyl isocyanide (0.079 g) and potassium carbonate (0.058 g) were added thereto, followed by heating to reflux for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 70-50% hexane/ethyl acetate] to obtain 0.56 g of methyl 2-(benzyloxy)-5-(oxazol-5-yl)benzoate as a light yellow solid.
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