Ammonium Chloride → (6-ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)methanol

HRID 1368539

반응식

HRID 1368539 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH3:14])[CH:8]=2)[CH:3]=1.[Mg].[CH:16]([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1)=[O:17].[Cl-].[NH4+]>C1COCC1.CI.O>[CH2:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:16]([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:22]=1)[OH:17])[CH:11]=[CH:10]2)[CH3:14]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 2368582-Bromo-6-ethoxynaphthaleneHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 5462224Magnesium2회

생성물 1

HCID 22664975(6-ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)methanol수율 59.6%

시약·촉매·용매 3

HCID 6328Methyl iodide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

2-Bromo-6-ethoxynaphthalene (5.3 g) was dissolved in THF (40 ml). To the solution were added magnesium (0.515 g) and methyl iodide (one drop), and the mixture was vigorously stirred to dissolve magnesium. The reaction mixture was cooled in ice bath, and a solution of 4-formyl-1-tritylimidazole (7 g) in THF (80 ml) was added dropwise over 30 min, and the mixture was stirred at room temperature for 1 h. To the reaction mixture were added saturated aqueous solution of ammonium chloride (40 ml) and water (40 ml), and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue was washed with ethyl acetate to give (6-ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)methanol (6.3 g) as a colorless powder. The product (6.3 g) was dissolved in dichloromethane (120 ml). To the solution was added manganese dioxide (6 g), and the mixture was stirred at room temperature over night. The reaction mixture was filtered with celite, and the filtrate was concentrated. The residue was crystallized from THF-ethyl acetate to give the titled compound (5.5 g) as a colorless powder.

후처리

  1. temperatureThe reaction mixture was cooled in ice bath
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washThe residue was washed with ethyl acetate

출처 및 근거

ORD 기록
ord-6b0eb481b39a4ca887c42308485e4fbe
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573289B1

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