Benzyl Alcohol → 4-(Benzyloxy)-2,6-dichloropyridine

HRID 594092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594092
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN1C(=O)CCC1>[CH2:18]([O:25][C:6]1[CH:7]=[C:2]([Cl:1])[N:3]=[C:4]([Cl:11])[CH:5]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 11430Potassium CarbonateHCID 38410702,6-Dichloro-4-nitropyridine

Produkt 1

HCID 582090464-(Benzyloxy)-2,6-dichloropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2,6-dichloro-4-nitropyridine (1.0 equiv.), potassium carbonate (2 equiv.) and benzyl alcohol (2.4 equiv.) in NMP (4 M) were heated to 90° C. for 2 h in the microwave. The mixture was partitioned between water and EtOAc. The organic phase was washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give crude 4-(benzyloxy)-2,6-dichloropyridine and was used in the next step without further purification. LCMS (m/z) (M+H)=254.0/256.0, Rt=1.05 min.

Aufarbeitung

  1. customThe mixture was partitioned between water and EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solution was concentrated
  5. customdried under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8781afdb645b4cd4a31147064cd3d3e5
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242969B2

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