Hydrochloric Acid → 5-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-imidazolidine-2,4-dione

Participants

Reaction Steps

A solution of crude 5-(2-hydroxy-ethyl)-3-(4-methyl-benzyl)-imidazolidine-2,4-dione (24.68 g, 99.4 mmol) and imidazole (10.15 g, 0.149 mol) in DMF (250 mL) was treated dropwise with tert-butyldiphenylsilyl chloride (27.37 g, 99.6 mmol) and then stirred at room temperature under N2 for 7 h. The reaction was worked up extractively with aqueous 1 N HCl (300 mL), diethyl ether and brine and the organic layer was dried (MgSO4) and the solvent removed in vacuo to give crude product which was purified by flash chromatography using a gradient of 5:1 to 2:1 hexanes:EtOAc to afford 23.82 g (49%) of 5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-imidazolidine-2,4-dione. MS (ES+) Calc'd for C29H35N2O3Si (M+1) 487. Found m/z 487 (100%). 1H NMR.

Provenance & Evidence