Thionyl Chloride → 2-(Chloromethyl)-5-methylpyridine

HRID 77894

Reaktionsgleichung

Reaktionsgleichung von HRID 77894
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 12325387(5-Methylpyridin-2-yl)methanol

Produkt 1

HCID 5880562-(Chloromethyl)-5-methylpyridineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixed solution of (5-methyl-pyridine-2-yl)-methanol (500 mg, 4.1 mmol) described in Manufacturing Example 11-1-1, thionyl chloride (0.59 mL, 8.1 mmol) and methylene chloride (10 mL) was stirred for 5 minutes under reflux. The reaction solution was cooled to room temperature and concentrated under a reduced pressure. The resulting residue was partitioned into diethyl ether and saturated sodium bicarbonate solution. The organic layer was separated and passed through a glass filter lined with silica gel (eluted with ethyl acetate). The eluate was concentrated to obtain the title compound (440 mg, 76%) as a crude product. The resulting compound was used in the following reaction without further purification.

Aufarbeitung

  1. temperatureunder reflux
  2. concentrationconcentrated under a reduced pressure
  3. customThe resulting residue was partitioned into diethyl ether and saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. filtrationfilter
  6. concentrationThe eluate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-0ce18b0b8ad34489bc176a56ffc7a334
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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