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

HRID 963699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963699
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 701861932-[(1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinoneAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2aa1f279f0c948a2ae7cc591a160b6cd
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763489

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