Boron trifluoride etherate → 6-Chloro-5-methylpyridin-3-ol

HRID 367066

Reaktionsgleichung

Reaktionsgleichung von HRID 367066
B(F)(F)F.CC[O:7][CH2:8][CH3:9].NC1[CH:12]=[C:13](C)[C:14]([Cl:17])=[N:15][CH:16]=1.N(OC(C)(C)C)=O.CCCCC>COCCOC>[Cl:17][C:14]1[C:13]([CH3:12])=[CH:9][C:8]([OH:7])=[CH:16][N:15]=1

Komponenten

6

Edukt 4

HCID 8000Boron trifluoride etherateHCID 8003PentaneHCID 10906Tert-Butyl nitriteHCID 122956076-Chloro-5-methylpyridin-3-amine

Produkt 1

HCID 128520156-Chloro-5-methylpyridin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel3×

Versuchsvorschrift

To a solution of boron trifluoride diethyl etherate (5.8 mL, 47.5 nmmol) in DME (18 mL) at -14° C. was added dropwise a solution of 5-amino-2-chloro-3-methylpyridine (4.5 g, 31.7 mmol) in DME (60 mL). The mixture was stirred for 15 minutes and then a solution of t-butyl nitrite (4.5 mL, 38 mmol) in DME (60 mL) was added dropwise. The mixture was stirred for 1 hour at 0° C., then pentane (100 mL) was added to give a solid. The solid was collected by filtration and dried to give the title compound (6.9 g): 1H NMR (MeOH-d4, 300 MHz) δ 2.58 (s, 3H), 8.86 (d, J=2.1 Hz, 1H), 9.41 (d, J=2.4 Hz, 1H).

Aufarbeitung

  1. stirringThe mixture was stirred for 1 hour at 0° C.
  2. customto give a solid
  3. filtrationThe solid was collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-98e5b069f27647238139caf236af52d5
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133253

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