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

HRID 1716827Notes

Reaction equation

[N:1]1([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][CH:19]=[C:20]([C:22](OC)=[O:23])[N:21]=3)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[O:18][CH:19]=[C:20]([CH2:22][OH:23])[N:21]=3)=[CH:15][CH:16]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: -10 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-92ccfaa96e9042d88b7a1cba3d5d6e41
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803825B2

Reaction notes

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