Water → 4-(2-Hydroxy-ethyl)-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one

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Reaction Steps

The 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one (16.79 g, assumed 27.8 mmol) was dissolved in THF (160 mL) and then treated with a 1 M solution of tetrabutylammonium fluoride in THF (55.6 mL, 55.5 mmol) and the reaction stirred at room temperature under N2 for 20 minutes. The reaction was worked up extractively with EtOAc and water and the organic layer dried (MgSO4) and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 3% of MeOH in CH2Cl2 to afford 4.65 g (61%) 4-(2-hydroxy-ethyl)-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one. MS (ES+) Calc'd for C16H23N2O2 (M+1) 275. Found m/z 275 (100%). 1H NMR.

Provenance & Evidence