Aluminium lithium hydride → {2-{4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazole-4-yl}methanol

HRID 1716831Notes

Reaction equation

HRID 1716831 reaction equation
[N:1]1([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][C:19]([CH3:26])=[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][C:19]([CH3:26])=[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

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57550214Methyl {2-{4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazol-4-yl}carboxylate

Product 1

HCID 57550209{2-{4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazole-4-yl}methanolYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl {2-{4-[(1H-benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazol-4-yl}carboxylate (0.093 g, 0.27 mmol) in dry THF was treated portionwise with LiAlH4 (0.020 g, 0.5 mmol) at 0° C., stirred for 1 h, quenched with ethyl acetate (0.5 mL) and water (0.2 mL), stirred for 30 min and filtered. The filtrate was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (silica, CH2Cl2:MeOH 95:5) to give the title compound as a white solid in 52% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 320 (MH+).

Workup

  1. customquenched with ethyl acetate (0.5 mL) and water (0.2 mL)
  2. stirringstirred for 30 min
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica, CH2Cl2:MeOH 95:5)

Sources & evidence

ORD record
ord-144540675d644406bf11da1f254006e9
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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