Реакция #1775

Уравнение реакции

HCl

ethyl 2-methylnicotinate

diisobutylaluminum hydride

NaOH

→

3-Hydroxymethyl-2-methylpyridine

Растворители

toluene

THF

Условия реакции

Обработка

1. 1
   Температураwarmed to ambient temperature
2. 2
   workup.WAITAfter 1 h
3. 3
   Температураthe solution was cooled in an ice bath
4. 4
   Другоеto quench
5. 5
   Другоеthe reaction
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеthe solvents were concentrated under reduced pressure
8. 8
   ДругоеThe resulting aqueous solution was partitioned between CHCl3 and saturated aqueous NaHCO3
9. 9
   ДругоеThe organic layer was separated
10. 10
    Промывкаthe aqueous layer was washed with additional CHCl3 (5×40 mL)
11. 11
    Сушкаdried (MgSO4)
12. 12
    Другоеevaporated under reduced pressure

Методика

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)).

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