反应详情

Acetyl pyridine (1.81 mL, 16.5 mmol) and methyl oxalate (3.12 g, 26.4 mmol) were dissolved in MeOH (30 mL, anhydrous). Sodium methoxide (6.9 mL, 25% in MeOH) was added over 10 min. Reaction solidified and was complete after 15 minutes. The solid mass was dissolved when acidified with HCl (10%, aqueous). The pH was then adjusted with NH4OH (conc) until precipitation ceased. The resulting solid was taken up in EtOAc. The aqueous layer was removed and extracted twice with EtOAc. The combined EtOAc layers were washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. Collected 1 (2.90 g, 85%) as an off-white solid.

1. customReaction
2. dissolutionThe solid mass was dissolved when
3. customThe pH was then adjusted with NH4OH (conc) until precipitation
4. customThe aqueous layer was removed
5. extractionextracted twice with EtOAc
6. washThe combined EtOAc layers were washed with water and brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customCollected 1 (2.90 g, 85%) as an off-white solid