Sodium hydride → HCID 71270138, Verbindung

HRID 927079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927079
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:16][C:17]1[N:18]=[N:19][C:20]([C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH2:32])=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O.O1CCCC1>[CH2:9]([O:16][C:17]1[N:18]=[N:19][C:20]([C:31]2([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:4][CH2:32]2)=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86677027HCID 86677027, Verbindung2×

Produkt 1

HCID 71270138HCID 71270138, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (0.487 g, 12.17 mmol, 60% in mineral oil) in DMSO (33.8 ml) stirring under nitrogen was added trimethyl sulfoxonium iodide (2.68 g, 12.17 mmol) in 4 portions over 20 minutes. A solution of 3,4-bis(benzyloxy)-6-(1-phenylethenyl)pyridazine (Intermediate 25; 3.2 g, 8.11 mmol) in tetrahydrofuran (50.7 ml) was added via a dropping funnel over 90 minutes before the reaction was left to stir at room temperature for 18 hours. The resulting mixture was concentrated, poured into ice water and extracted with ethyl acetate (×3). The organics portion was dried (MgSO4), filtered and concentrated to give a brown oil. The crude oil was purified by silica chromatography (eluting with 0-50% ethyl acetate in petrol) to yield 3,4-bis(benzyloxy)-6-(1-phenylcyclopropyl)pyridazine as a yellow oil (yield=23%).

Aufarbeitung

  1. waitwas left
  2. stirringto stir at room temperature for 18 hours
  3. concentrationThe resulting mixture was concentrated
  4. additionpoured into ice water
  5. extractionextracted with ethyl acetate (×3)
  6. dry with materialThe organics portion was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown oil
  10. customThe crude oil was purified by silica chromatography (eluting with 0-50% ethyl acetate in petrol)

Quellen und Nachweise

ORD-Eintrag
ord-7ba4e5423ab94d1f85fbed25495a5411
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290456B2

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