1-(5-Ethenyl-6-methoxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol → HCID 178437262, compound

HRID 1368546Notes

Reaction equation

HRID 1368546 reaction equation
[CH:1]([C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:15]([C:20]1[N:21]=[CH:22][N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:24]=1)([OH:19])[CH:16]([CH3:18])[CH3:17])=[CH:8]2)=[CH2:2]>CO.C1COCC1.[C].[Pd]>[CH2:1]([C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:15]([C:20]1[N:21]=[CH:22][NH:23][CH:24]=1)([OH:19])[CH:16]([CH3:18])[CH3:17])=[CH:8]2)[CH3:2]

Participants

5

Reactant 1

HCID 220183661-(5-Ethenyl-6-methoxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol

Product 1

HCID 178437262HCID 178437262, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(5-Ethenyl-6-methoxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol (1.28 g) was dissolved in a mixture of methanol and THF (1:1, 50 ml). To the solution was added 10% palladium carbon (0.3 g), and the mixture was stirred at room temperature for 2 h under hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated. The residue was dissolved in a mixed solution of methanol and THF (3:1, 40 ml). To the solution was added pyridine hydrochloride (0.65 g), and the mixture was stirred at 60° C. for 3 h. The reaction mixture was concentrated to dryness, and to the residue were added ethyl acetate and 1N-hydrochloric acid (20 ml). The organic layer was extracted four times with 1N-hydrochloric acid. The aqueous layer was neutralized with an aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried and concentrated. The residue was purified by silica gel chromatography (eluent, dichloromethane-methanol=10:1) followed by crystallization from dichloromethane-diisopropyl ether-hexane to give the titled compound (0.49 g) as a colorless powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in a mixed solution of methanol and THF (3:1, 40 ml)
  4. additionTo the solution was added pyridine hydrochloride (0.65 g)
  5. stirringthe mixture was stirred at 60° C. for 3 h
  6. concentrationThe reaction mixture was concentrated to dryness
  7. additionto the residue were added ethyl acetate and 1N-hydrochloric acid (20 ml)
  8. extractionThe organic layer was extracted four times with 1N-hydrochloric acid
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated sodium chloride solution
  11. customdried
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel chromatography (eluent, dichloromethane-methanol=10:1)
  14. customfollowed by crystallization from dichloromethane-diisopropyl ether-hexane

Sources & evidence

ORD record
ord-690dfcee575341db93a63b69904c4e10
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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