Sodium hydride → 2-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

HRID 344033노트

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HRID 344033 반응식
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1(C)C=CC(S(O[CH2:33][CH:34]2[CH2:43][CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][C:40]=3[O:44][CH3:45])[CH2:35]2)(=O)=O)=CC=1>CN(C)C=O>[CH3:45][O:44][C:40]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:41]=1[CH2:42][CH2:43][CH:34]([CH2:33][N:12]1[C:11](=[O:14])[CH:10]=[CH:9][C:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:13]1)[CH2:35]2

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 11739484(5-Methoxy-1,2,3,4-tetrahydro-2-naphthyl)methyl p-toluenesulfonateHCID 543237696-diphenylmethyl-3(2H)-pyridazinone

생성물 1

HCID 701861932-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone수율 63.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

A suspension of 6-diphenylmethyl-3(2H)-pyridazinone (0.58 g) and sodium hydride (60%, 110 mg) in dry N,N-dimethylformamide (7 ml) was stirred at 0° C. for 30 minutes. A solution of (5-methoxy-1,2,3,4-tetrahydro-2-naphthyl)methyl p-toluenesulfonate (0.77 g) in dry N,N-dimethylformamide (5 ml) was added dropwise to the suspension at room temperature. The mixture was stirred for 6 hours and poured into ice-1N hydrochloric acid and extracted with ethyl acetate. The extract was separated, washed with water (twice) and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate =5:1~3:1) to give 2-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.61 g) as a pale yellow oil.

후처리

  1. stirringThe mixture was stirred for 6 hours
  2. extractionextracted with ethyl acetate
  3. customThe extract was separated
  4. washwashed with water (twice) and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane: ethyl acetate =5:1~3:1)

출처 및 근거

ORD 기록
ord-441f462888e4402cb0c26de474f8cc0c
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863918

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