Aluminium lithium hydride → 1-Trityl-1H-benzimidazol-5-yl-methanol

HRID 1815440

Reaction equation

HRID 1815440 reaction equation
C[O:2][C:3]([C:5]1[CH:32]=[CH:31][C:8]2[N:9]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:12]([N:9]1[C:8]2[CH:31]=[CH:32][C:5]([CH2:3][OH:2])=[CH:6][C:7]=2[N:11]=[CH:10]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22710354methyl N-triphenylmethyl-5-benzimidazolecarboxylate

Product 1

HCID 230215391-Trityl-1H-benzimidazol-5-yl-methanolYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled stirred suspension of the product of step b (3.61 g, 7.94 mmol) in THF (30 ml) was added dropwise a solution of lithium aluminium hydride (1.0M in THF, 10 ml, 10.0 mmol). The suspension was stirred at this temperature for 1 h and then was quenched with saturated aqueous ammonium chloride (100 ml). The aqueous solution was extracted thrice with ethyl acetate (100 ml) and the combined organic phases were washed with brine (200 ml). The organic phase was dried over magnesium sulfate and the filtrate was evaporated at reduced pressure and the residue recrystallised from ethyl acetate/hexane to afford the title compound (2.68 g, 79%). 1H NMR 7.89 (1H, s), 7.74 (1H, d, 8.4), 7.33-7.17 (17H, m), 6.44 (1H, d, 0.9), 4.45 (2H, d, 6), 1.37 (1H, t, 6).

Workup

  1. stirringThe suspension was stirred at this temperature for 1 h
  2. customwas quenched with saturated aqueous ammonium chloride (100 ml)
  3. extractionThe aqueous solution was extracted thrice with ethyl acetate (100 ml)
  4. washthe combined organic phases were washed with brine (200 ml)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe filtrate was evaporated at reduced pressure
  7. customthe residue recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f7028a4a76bc44408a4da8a12b785a80
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Linked notes

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