Reaktion #71634

Reaktionsgleichung

2-bromo-5-formylpyridine

methyl acrylate

tri-(o-tolyl)phosphine

sodium acetate

→

title compound

Ausbeute 93.7%

Ethyl (2E)-3-(5-formyl-2-pyridinyl)-2-propenoate

Ausbeute 93.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through Celite®
2. 2
   workup.ADDITIONthen diluted with DCM and water
3. 3
   SonstigeThe organic phase was dried
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigepurified by chromatography

Vorschrift

A mixture of 2-bromo-5-formylpyridine (500 mg, 2.6 mmol), methyl acrylate (0.6 ml, 6.5 mmol), tri-(o-tolyl)phosphine (80 mg, 0.26 mmol), allyl palladium (II) chloride dimer (47 mg, 0.13 mmol) and sodium acetate (1.08 g, 8 mmol) in DMF (10 ml) was heated at 170° C. in a microwave reactor for 0.75 h. The reaction mixture was filtered through Celite® then diluted with DCM and water. The organic phase was dried, concentrated in vacuo and purified by chromatography to give the title compound as a white solid (50 mg). δH (CDCl3, 250 MHz) 10.14 (1H, s), 9.09 (1H, d), 8.19 (1H, dd), 7.72 (1H, d), 7.57 (1H, d), 7.08 (1H, d), 3.85 (3H, s). MS (ES): MH+ 192.

Quelle