Hydrochloric Acid → α-Phenyl-1H-imidazole-5-methanol

HRID 1694787Notes

Reaction equation

HRID 1694787 reaction equation
Cl.CN(C)S([N:7]1[CH:11]=[C:10]([CH:12]([OH:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=[C:8]1[Si](C(C)(C)C)(C)C)(=O)=O>CO>[OH:19][CH:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:10]1[NH:9][CH:8]=[N:7][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58951927HCID 58951927, compound

Product 1

HCID 15082952α-Phenyl-1H-imidazole-5-methanolYield 28.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A gentle stream of HCl gas was bubbled through a refluxing solution of 2-(tert-butyl-dimethyl-silanyl)-4-(hydroxy-phenyl-methyl)-imidazole-1-sulfonic acid dimethylamide (0.2 g, 0.51 mmol) in methanol (5 ml) for 1 hour. The solvent was evaporated and sodium hydroxide solution was added. The mixture was extracted with dichloromethane (2 times). The combined organic layers are dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1) to yield 25 mg (26%) of rac-5-(hydroxy-phenyl-methyl)-1H-imidazole, MS (EI): 174.1 ((M+.) and 5 mg (5%) of rac-5-(methoxy-phenyl-methyl)-1H-imidazole as colourless oil: MS (ISP): 189.1 ((M+H)+.).

Workup

  1. customThe solvent was evaporated
  2. additionsodium hydroxide solution was added
  3. extractionThe mixture was extracted with dichloromethane (2 times)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1)

Sources & evidence

ORD record
ord-1cc8a51e2df0438ab325748bc1123a2a
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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