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

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+).

1. customquenched with water and 10% sodium hydroxide solution
2. customThe phases were separated
3. extractionthe aqueous phase was extracted with ethyl acetate
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over Na2SO4
6. customevaporated to dryness

ORD-Eintrag

ord-92ccfaa96e9042d88b7a1cba3d5d6e41

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07803825B2