Sodium periodate → 2-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazole-7-carbaldehyde

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Reaction Steps

To a solution of 3-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)isoxazole (Preparation 56E, 0.350 g, 0.825 mmol) in THF (7.5 ml) at room temperature, was added a solution of osmium tetroxide, (2.5% in butanol, 1.7 ml, 0.017 mmol) followed by sodium periodate (0.265 g, 1.238 mmol) as a solution in 7.5 ml of water. After stirring for 90 min it was quenched with a saturated solution of sodium bisulfate. The dark colored suspension was filtered through Celite. The filter cake was washed with EtOAc. The combined EtOAc layers were washed with water, dried over anhydrous MgSO4, concentrated, and chromatographed to yield the 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazole-7-carbaldehyde as an orange colored solid. The product had an LC ret. time=3.136 min. (condition: Start % B=50, Final % B=100, Gradient Time=4 min, Flow Rate=4 ml/min, Wavelength=220, Solvent Pair=MeOH−H2O−TFA; Solvent A=10% MeOH−90% H2O−0.1% TFA; Solvent B=90% MeOH−10% H2O−0.1% TFA; Column 1=1: Waters Sunfire C18 4.6×50 mm (4 min. grad)); LC/MS M+1=427.03.

Provenance & Evidence