5-Methyl-1,3-dioxane-5-methanol → 3-Methoxy-2-methyl-4-(5-methyl-1,3-dioxan-5-yl-methoxy)pyridine-N-oxide

HRID 1647173

Reaktionsgleichung

Reaktionsgleichung von HRID 1647173
[OH:1][CH2:2][C:3]1([CH3:9])[CH2:8][O:7][CH2:6][O:5][CH2:4]1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][N+:16]([O-:19])=[C:15]([CH3:20])[C:14]=1[O:21][CH3:22]>C1COCC1>[CH3:22][O:21][C:14]1[C:15]([CH3:20])=[N+:16]([O-:19])[CH:17]=[CH:18][C:13]=1[O:1][CH2:2][C:3]1([CH3:9])[CH2:8][O:7][CH2:6][O:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 142785-Methyl-1,3-dioxane-5-methanolHCID 24758Sodium hydrideHCID 5083929Pyridine, 4-chloro-3-methoxy-2-methyl-, 1-oxide

Produkt 1

HCID 199264413-Methoxy-2-methyl-4-(5-methyl-1,3-dioxan-5-yl-methoxy)pyridine-N-oxideAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A deareated solution of 5-(hydroxymethyl)-5-methyl-1,3-dioxane (1.19 g, 9 mmol) in 125 ml dry THF was treated with NaH (0.79 g 55% dispersion in oil, 18 mmol) for 20 min. 4-Chloro-3-methoxy-2-methylpyridine-N-oxide (1.04 g, 6 mmol) was added and the mixture was refluxed for 26 h. Excess NaH was quenched with 10 ml of H2O and the solvent evaporated. The residue was partitioned between 150 ml CH2Cl2 and 50 ml 5% Na2CO3. The organic layer was passed through a phase separation paper and evaporated leaving 1.83 g enriched product. Chromatography (SiO2CH2Cl2 /MeOH, 95/5) afforded 0.39 g (24%) pure title compound as a tanned oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 26 h
  2. customExcess NaH was quenched with 10 ml of H2O
  3. customthe solvent evaporated
  4. customThe residue was partitioned between 150 ml CH2Cl2 and 50 ml 5% Na2CO3
  5. customThe organic layer was passed through a phase separation paper
  6. customevaporated
  7. customleaving 1.83 g

Quellen und Nachweise

ORD-Eintrag
ord-74b8ce39ae504535910b2f3364759b16
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05430042

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