Triethylamine → 3-Methanesulfonyl-pyridine

HRID 902007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902007
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C1COCC1.O>[CH3:20][S:21]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:23])=[O:22]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 31297Methanesulfonyl chlorideHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 4168063-Methanesulfonyl-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-bromopyridine (20 g, 127 mmol) in THF (200 ml) at room temperature is added a solution of 2M isopropylmagnesium chloride in THF (64 ml, 127 mmol). The resulting mixture is stirred for 2 hours, treated with triethylamine (20 ml), immediately followed by methanesulfonylchloride (10 ml, 127 mmol) and the resulting mixture stirred for 18 hours at room temperature. The mixture is diluted with water (200 ml) and extracted with EtOAc (3×100 ml). The mixture is concentrated in vacuo and purified on Silica gel (eluting with 50/50 Hexane/EtOAc). 1H-NMR (CDCl3) δ: 9.17 (s, 1H), 8.90 (d, 1H), 8.25 (dd, 1H), 7.55 (m, 1H), 3.12 (s, 3H).

Aufarbeitung

  1. stirringthe resulting mixture stirred for 18 hours at room temperature
  2. extractionextracted with EtOAc (3×100 ml)
  3. concentrationThe mixture is concentrated in vacuo
  4. custompurified on Silica gel (eluting with 50/50 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-61df36c7a60b44f5a29b7362d13e19de
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365066B2

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