Triethylsilane → HCID 118324012, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)(thiazol-2-yl)methanol (33 mg, 0.0732 mmol) and triethylsilane (0.035 mL, 0.22 mmol) in CH2Cl2 (2 mL) at −78° C. was added dropwise TiCl4 (0.22 mL, 0.22 mmol). The resulting mixture (turned to dark green suspension) was kept at −78° C. for 20 min and then warmed to 0° C. The reaction was maintained at 0° C. for 1 hr and then quenched with ice, CH2Cl2 and aqueous NaOH until the aqueous layer became basic. The aqueous layer was extracted with CH2Cl2 twice. The combined organics were concentrated and purified by chromatography (silica column, 25% EtOAc/CH2Cl2) to yield (E)-2-((4-methoxyphenyl)(4-styrylquinolin-6-yl)methyl)thiazole.

Provenance & Evidence