1,2-Dichloroethane → Ethyl 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazole-5-carboxylate

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Reaction Steps

To a 500 ml round-bottom flask equipped with a magnetic stir-bar was mixed ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-chloro-3-oxobutanoate (20.4 g, 52.88 mmoles, 1 eq), 4-trifluoromethylthiobenzamide (12.2 g, 59.5 mmoles, 1.1 eq), 1,2-dichloroethane (150 ml, 0.44M) and H2O (3 ml). This mixture was refluxed for 12 hrs. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (100 ml) and washed with sat. NaHCO3. Once the phases were separated, the organic phase was washed with water, brine and dried over Na2SO4. This was then filtered, concentrated in vacuo and purified via silica gel chromatography (5% EtOAc/Hexanes to 20% EtOAc/Hexanes) to yield 20.3 g (76%) of the titled compound.

Provenance & Evidence