반응 #1775

반응 방정식

HCl

ethyl 2-methylnicotinate

diisobutylaluminum hydride

NaOH

→

3-Hydroxymethyl-2-methylpyridine

용매

toluene

THF

반응 조건

후처리

1. 1
   온도warmed to ambient temperature
2. 2
   workup.WAITAfter 1 h
3. 3
   온도the solution was cooled in an ice bath
4. 4
   기타to quench
5. 5
   기타the reaction
6. 6
   여과filtered
7. 7
   농축the solvents were concentrated under reduced pressure
8. 8
   기타The resulting aqueous solution was partitioned between CHCl3 and saturated aqueous NaHCO3
9. 9
   기타The organic layer was separated
10. 10
    세척the aqueous layer was washed with additional CHCl3 (5×40 mL)
11. 11
    건조dried (MgSO4)
12. 12
    기타evaporated under reduced pressure

실험 절차

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)).

출처