Potassium Acetate → methyl-4-[(2-butyl-5-formyl-1H-imidazol-1-yl)-methyl]naphthalene-1-carboxylate

HRID 37006Notes

Reaction equation

HRID 37006 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][N:16]2[C:20]([CH:21]=[O:22])=[C:19](I)[N:18]=[C:17]2[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:7][CH:6]=1)=[O:4].C([O-])(=O)C.[K+]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][N:16]2[C:20]([CH:21]=[O:22])=[CH:19][N:18]=[C:17]2[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 517044Potassium Acetate2×HCID 19936811methyl-4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]naphthalene-1-carboxylate

Product 1

HCID 15231321methyl-4-[(2-butyl-5-formyl-1H-imidazol-1-yl)-methyl]naphthalene-1-carboxylateYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 40.0 g (83.9 mmol) of methyl-4-[(2-Butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]naphthalene-1-carboxylate, 9.07 g (92.4 mmol) of potassium acetate, and 6.0 g of 10% palladium on carbon in 1.2 liters of ethyl acetate was hydrogenated for 2 hours. The solids were removed by filtration and an additional 8.0 g of 10% palladium on carbon and 9.01 g (92.4 mmol) of potassium acetate was added. After hydrogenating the reation mixture an additional 2 hours, the solids were removed by filtration and the solution was concentrated to about 1/3 volume. The ethyl acetate solution was washed with aqueous sodium carbonate solution, dried over magnesium sulfate, and concentrated under vacuum to give an oil which crystallized. Recrystallization from methylene chloride-hexane gave 25.77 g (87.6%) of colorless crystals; mp 95.5°-97° C.

Workup

  1. customThe solids were removed by filtration
  2. customan additional 2 hours
  3. customthe solids were removed by filtration
  4. concentrationthe solution was concentrated to about 1/3 volume
  5. washThe ethyl acetate solution was washed with aqueous sodium carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customto give an oil which
  9. customcrystallized
  10. customRecrystallization from methylene chloride-hexane

Sources & evidence

ORD record
ord-e2ff24a23ddc4ee999a57b8f048e2ab4
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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