p-Toluenesulfonic acid → 2-Methoxy-5-((tetrahydro-2H-pyran-2-yl)oxy)pyridine

HRID 56750

Reaktionsgleichung

Reaktionsgleichung von HRID 56750
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:18][O:19][C:20]1[N:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.O.ClCCl>ClCCl>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)=[CH:24][N:25]=1

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 116223355-Hydroxy-2-methoxypyridineHCID 21908982Water methylene chloride

Produkt 1

HCID 1176226612-Methoxy-5-((tetrahydro-2H-pyran-2-yl)oxy)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10.1 g (119.9 mmol, 1.5 eq.) of 3,4-dihydro-2H-pyran and 1.4 g (8.0 mmol, 0.1 eq.) of 4-toluenesulphonic acid were added to a solution of 10.0 g (79.9 mmol) of 6-methoxypyridin-3-ol in 150 ml of dichloromethane, and the mixture was stirred at RT for 5 d. After addition of water/dichloromethane and phase separation, the aqueous phase was extracted with dichloromethane. The combined organic phases were dried (sodium sulphate), filtered and concentrated under reduced pressure. Yield: 17.3 g (100% of theory)

Aufarbeitung

  1. extractionthe aqueous phase was extracted with dichloromethane
  2. dry with materialThe combined organic phases were dried (sodium sulphate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6770c83df914ad7bc6d1b64050071cf
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434690B2

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