Aluminium lithium hydride → {2-[4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-1,3-oxazole-4-yl]methanol

Participants

Reaction Conditions

Reaction Steps

A solution of methyl {2-{4-[(1H-benzimidazol-1-yl)methyl]phenyl}-1,3-oxazol-4-yl}carboxylate (0.1 g, 3 mmol) in THF was added dropwise at −10° C. to a suspension of LiAlH4 (0.011 g, 3 mmol) in dry THF. The reaction mixture was stirred for one hour at −10° C. and quenched with water and 10% sodium hydroxide solution. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness to give the title product in 76% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, CDCl3): 8.00 (s, 1H), 7.98 (d, J=8 Hz, 2H), 7.78 (d, J=14 Hz, 1H), 7.67 (s, 1H), 7.55 (s, 1H), 7.2 (m, 5H), 5.4 (s, 2H), 4.59 (s, 2H). LCMS (ESI+) 306 (MH+).

Provenance & Evidence