ChemicalBook CAS DataBase List 2-Hexylpyridine

2-Hexylpyridine synthesis

14synthesis methods

Product Name:2-Hexylpyridine
CAS Number:1129-69-7
Molecular formula:C11H17N
Molecular Weight:163.26

109-09-1
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$10.60/1gm:

44767-62-6
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1129-69-7
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$31.00/250mg

Yield:1129-69-7 86 %Spectr.

Reaction Conditions:

Stage #1: 2-chloropyridinewith MnCl₂(THF)_1.6 in tetrahydrofuran at 21; for 0.0833333 h;Glovebox;Inert atmosphere;Kumada Cross-Coupling;
Stage #2: n-hexylmagnesium chloride in tetrahydrofuran at 21; for 24 h;Glovebox;Inert atmosphere;Kumada Cross-Coupling;

Steps:

D. General Procedure for Mn-catalyzed cross-coupling of halopyridines

General procedure: 20 mL scintillation vial was charged with a solution of MnCl2THF1.6 (3 mol%, 3 mg, 0.012mmol) in 3 mL THF in a glove box. The corresponding electrophile (0.41 mmol, 1 equiv.) andinternal standard, mesitylene (0.41 mmol, 1equiv.), were added. After five minutes of stirring atroom temperature, the Grignard solution (1.2- 2.6 equiv.) was added dropwise and the reactionwas stirred at room temperature. The reaction mixture was removed from the glovebox andquenched with a saturated K2CO3 solution (3 mL) and EtOAc (3 mL). The organic layer wasextracted with EtOAc (3 x 3mL), and dried over MgSO4. The solution was then filtered andconcentrated. The crude product was purified via a silica plug.

References:

Petel, Brittney E.;Purak, Merjema;Matson, Ellen M. [Synlett,2018,vol. 29,# 13,p. 1700 - 1706] Location in patent:supporting information