Reaktion #1775

Reaktionsgleichung

HCl

ethyl 2-methylnicotinate

diisobutylaluminum hydride

NaOH

→

3-Hydroxymethyl-2-methylpyridine

Lösungsmittel

toluene

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed to ambient temperature
2. 2
   workup.WAITAfter 1 h
3. 3
   Temperaturthe solution was cooled in an ice bath
4. 4
   Sonstigeto quench
5. 5
   Sonstigethe reaction
6. 6
   Filtrationfiltered
7. 7
   Einengenthe solvents were concentrated under reduced pressure
8. 8
   SonstigeThe resulting aqueous solution was partitioned between CHCl3 and saturated aqueous NaHCO3
9. 9
   SonstigeThe organic layer was separated
10. 10
    Waschenthe aqueous layer was washed with additional CHCl3 (5×40 mL)
11. 11
    Trocknendried (MgSO4)
12. 12
    Sonstigeevaporated under reduced pressure

Vorschrift

To a stirred solution of ethyl 2-methylnicotinate (1.50 g, 9.09 mmol) in freshly distilled THF (100 mL) at 0° C. was added diisobutylaluminum hydride (11.2 mL of a 1.5M solution in toluene, 16.9 mmol). The solution was stirred for 6 h at 0° C. and then warmed to ambient temperature. After 1 h, the solution was cooled in an ice bath and 1N HCl (75 mL) was added to quench the reaction. The mixture was made alkaline with aqueous NaOH (pH=8.5), filtered, and the solvents were concentrated under reduced pressure. The resulting aqueous solution was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was separated, and the aqueous layer was washed with additional CHCl3 (5×40 mL). The organic layers were combined, dried (MgSO4), and evaporated under reduced pressure. 3-Hydroxymethyl-2-methylpyridine was obtained as a slightly amber oil and was used in the next step without purification (TLC: Rf =0.40 (5% MeOH:CH2Cl2)).

Quelle