反応 #1775

反応方程式

HCl

ethyl 2-methylnicotinate

diisobutylaluminum hydride

NaOH

→

3-Hydroxymethyl-2-methylpyridine

溶媒

toluene

THF

反応条件

後処理

1. 1
   温度warmed to ambient temperature
2. 2
   workup.WAITAfter 1 h
3. 3
   温度the solution was cooled in an ice bath
4. 4
   その他to quench
5. 5
   その他the reaction
6. 6
   ろ過filtered
7. 7
   濃縮the solvents were concentrated under reduced pressure
8. 8
   その他The resulting aqueous solution was partitioned between CHCl3 and saturated aqueous NaHCO3
9. 9
   その他The organic layer was separated
10. 10
    洗浄the aqueous layer was washed with additional CHCl3 (5×40 mL)
11. 11
    乾燥dried (MgSO4)
12. 12
    その他evaporated under reduced pressure

実験手順

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)).

出典