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

HRID 37006노트

반응식

HRID 37006 반응식
[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]

참가 물질

5

반응물 2

HCID 517044Potassium Acetate2회HCID 19936811methyl-4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]naphthalene-1-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e2ff24a23ddc4ee999a57b8f048e2ab4
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418250

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