6-(2-Benzyloxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one → 6-(2-Hydroxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one

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Reaction Steps

A mixture of 6-(2-benzyloxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one (0.69 g, 2.31 mmol) and 20% palladium on carbon (0.10 g) in methanol (10 ml) and tetrahydrofuran (10 ml) was stirred under a hydrogen atmosphere (1 atm) for 2 h. After removal of the catalyst, the catalyst was washed with boiling methanol (50 ml). The filtrate was evaporated to give 6-(2-hydroxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one (0.46 g, 96%) as a solid. 1H NMR (DMSO) 10.54 (1H, s), 6.78 (1H, d, J=8.3), 6.70 (H, d, J=632.2), 6.50 (1H, dd, J=8.3, 2.4), 4.79 (1H, t, J=5.6), 3.90 (2H, t, J=5.0), 3.64 (2H, q, J=5.2), 3.18 (3H, s).

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