Sodium hydride → [4-(4-[1,2,3]triazol-1-yl-butyl)phenyl]-{2-[(E)-2-(-4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester

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Reaction Steps

To an ice-cold solution of [4-(4-[1,2,3]triazol-1-yl-butyl)phenyl]-carbamic acid tert-butyl ester (188 mg, 0.6 mmol) in N,N-dimethylformamide (5 ml) was added sodium hydride (16.5 mg, 0.65 mmol) and the mixture stirred for 30 min. After addition of 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole (200 mg, 0.6 mmol), the mixture was stirred at room temperature over night, then mixed with 40 ml ammonium chloride solution, thoroughly extracted with ethyl acetate and the extract dried and evaporated. Flash column chromatography (ethyl acetate/heptane 2:1) yielded 105 mg (29%) [4-(4-[1,2,3]triazol-1-yl-butyl)phenyl]-{2-[(E)-2-(−4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester as oily residue.

Provenance & Evidence