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

HRID 2081873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2081873
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 15231321methyl-4-[(2-butyl-5-formyl-1H-imidazol-1-yl)-methyl]naphthalene-1-carboxylateAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e2e93c2330d64887bb7c294dd741cdfd
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05185351

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