Water → (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 22 (2.5 g, 9.61 mmol) in anhydrous THF (10 mL) was added dropwise to a mixture of LiAlH4 (0.55 g, 14.42 mmol) in anhydrous THF (20 mL) at 0° C. under nitrogen. The reaction mixture was stirred for 30 min at 0° C. then treated sequentially with water (2 mL) and 10% NaOH (1.8 mL). The resulting mixture was extracted with ether (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford 2.24 g (95%) of (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol (24) as yellow oil: MS (ESI) m/z=233.2 [M+1]+.

Provenance & Evidence