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Diisobutylaluminumhydride → [2-(3-Methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-yl]methanol

HRID 1176545
Notes
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Reaction equation

HRID 1176545 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]2[CH:29]=[CH:30][CH:31]=[C:32]([C:33](OC)=[O:34])[C:18]=2[N:17]=1>O1CCCC1>[CH3:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[C:19]2[CH:29]=[CH:30][CH:31]=[C:32]([CH2:33][OH:34])[C:18]=2[N:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68502641Methyl 2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazole-4-carboxylate

Product 1

HCID 68503680[2-(3-Methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

35 ml of diisobutylaluminium hydride (1.5M in toluene) are added dropwise at −70° C. to a solution of 4.95 g of methyl 2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazole-4-carboxylate in 200 ml of tetrahydrofuran. The reaction mixture is then stirred at −10° C. for 1 hour and subsequently partitioned between tert-butyl methyl ether and 2:1 water/1N potassium bisulphate solution—the organic phase is washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulphate and concentrated by evaporation. The combined aqueous phases are reextracted with ethyl acetate (3×)—the combined organic phases are washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residues by means of flash chromatography (SiO2 60F). Rf=0.21 (95:5 ethyl acetate-methanol); Rt=3.91.

Workup

  1. customsubsequently partitioned between tert-butyl methyl ether and 2:1 water/1N potassium bisulphate solution—the organic phase
  2. washis washed with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. washare washed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fc4d1b89c33f45a885cd14b23d8a19e4
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842688B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes