Hydrochloric Acid → alpha-Ethyl-1-(triphenylmethyl)-1H-imidazole-4-methanol

HRID 2043619Notes

Reaction equation

HRID 2043619 reaction equation
[CH2:1](I)[CH3:2].[Li]C(C)(C)C.CCCCC.[C:14]([N:33]1[CH:37]=[C:36]([CH:38]=[O:39])[N:35]=[CH:34]1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>CCOCC.C1COCC1>[C:14]([N:33]1[CH:37]=[C:36]([CH:38]([OH:39])[CH2:1][CH3:2])[N:35]=[CH:34]1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 8003PentaneHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 12344795alpha-Ethyl-1-(triphenylmethyl)-1H-imidazole-4-methanolYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 100 ml, three-necked flask fitted with a magnetic stirrer, under inert atmosphere, ethyl iodide (1.1 ml, 0.0136 mol) is dissolved in Et2O (25 ml). At −70° C., a 1.5 M solution of t-BuLi in pentane (17 ml, 0.026 mol) is added dropwise. The mixture is stirred 0.3 h at this temperature and 0.75 h at room temperature. A solution of 1-trityl-1H-imidazole-4-carbaldehyde x43 (2 g, 0.00591 mole) in THF (25 ml) is added dropwise at 0° C. The mixture is stirred for 1 h and poured onto ice. HCl is added until the pH is slightly acid (pH: 3-5) and the aqueous phase is extracted twice with Et2O. The combined organic phases are dried over MgSO4, filtered and concentrated to dryness. The crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 95/4.5/0.5 (v/v/v)) to afford 1.21 g of 1-(1-trityl-1H-imidazol-4-yl)propan-1-ol x88.

Workup

  1. stirringThe mixture is stirred for 1 h
  2. additionpoured onto ice
  3. extractionthe aqueous phase is extracted twice with Et2O
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 95/4.5/0.5 (v/v/v))

Sources & evidence

ORD record
ord-4f0d56021fef4c03920f2b9475ce1b2e
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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