Hydrochloric Acid → 1-(1H-Imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)ethanol

HRID 1368512Notes

Reaction equation

HRID 1368512 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([C:16]1[N:17]=[CH:18][N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:20]=1)([OH:15])[CH3:14])[CH:7]=[CH:6]2.Cl>C(O)=O>[NH:19]1[CH:20]=[C:16]([C:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)([OH:15])[CH3:14])[N:17]=[CH:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 220183271-(6-Methoxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)ethanol

Product 1

HCID 1784874671-(1H-Imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)ethanolYield 90.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-(6-Methoxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)ethanol (2.20 g) was dissolved in 90% formic acid (15 ml), and the solution was stirred at room temperature for 15 h. To the solution was added 1 N-hydrochloric acid, and precipitate was filtered off. The filtrate was neutralized with potassium carbonate, and extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:methanol=20:1 chloroform:methanol=10:1) to give the titled compound (1.05 g) as a colorless solid.

Workup

  1. filtrationwas filtered off
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous solution of sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:methanol=20:1 chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-eba82464524843c791f64b7490cbf885
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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