Reaktion #470949

Reaktionsgleichung

Sodium hydride

trimethylphosphonoacetate

THF

1-pyridin-3-ylethanone

→

title compound

methyl 3-pyridin-3-ylbut-2-enoate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   workup.ADDITIONpoured
4. 4
   Extraktionaq. NH4Cl and extracted with EtOAc
5. 5
   WaschenThe combined organics were washed with brine
6. 6
   Trocknendried (sodium sulfate)
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigePurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-60% EtOAc/hexanes as eluent)

Vorschrift

Sodium hydride (192 mg of a 60% wt. suspension, 4.80 mmol) was added in several portions to a stirred solution of trimethylphosphonoacetate (712 μL, 4.40 mmol) in THF (20.0 mL). After 5 min, 1-pyridin-3-ylethanone (440 μL, 4.00 mmol) was added dropwise, and the resulting mixture was heated to reflux. After 20 h, the reaction mixture was cooled to rt, poured into said. aq. NH4Cl and extracted with EtOAc. The combined organics were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-60% EtOAc/hexanes as eluent) afforded the title compound i-8a as a separable mixture of two isomers. m/z (ES) 178 (MH)+.

Quelle