Reaktion #47094

Reaktionsgleichung

ethyl bromoacetate

sodium hydride

2-pyridone

→

product 425

Ausbeute 76.2%

(2-Oxo-2H-pyridin-1-yl)acetic acid ethyl ester

Ausbeute 76.2%

Lösungsmittel

THF

THF

DMPU

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction is quenched with water
2. 2
   Extraktionextracted with EtOAc
3. 3
   SonstigeThe organic layer is separated
4. 4
   Sonstigeevaporated
5. 5
   Sonstigethe residue purified by chromatography on silica gel
6. 6
   Waschenelution with EtOAC

Vorschrift

To a suspension of 60% sodium hydride dispersion in mineral oil (220 mg, 5.5 mmol) in cold (0° C.) THF is added 2-pyridone (475 mg, 5.0 mmol) in THF (4 mL) and DMPU (2 mL) followed by ethyl bromoacetate (0.556 mL, 5.0 mmol), and the reaction is stirred at RT for 1 h. The reaction is quenched with water, and extracted with EtOAc. The organic layer is separated, evaporated, and the residue purified by chromatography on silica gel; elution with EtOAC:dichloromethane:heptane (50:30:20) gives 690 mg of the product 425. 1H NMR (CDCl3) δ 7.35 (m, 1H), 7.21 (d, 1H), 6.57 (d, 1H), 6.19 (t, 1H), 4.62 (s, 2H), 4.23 (q, 2H), 1.28 (t, 3H); MS: m/z 182 (M++1).

Quelle