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

HRID 37006ノート

反応式

HRID 37006 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2ff24a23ddc4ee999a57b8f048e2ab4
出典データセット
uspto-grants-1995_05
特許番号
US05418250

反応ノート

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