反応 #71634

反応方程式

2-bromo-5-formylpyridine

methyl acrylate

tri-(o-tolyl)phosphine

sodium acetate

→

title compound

収率 93.7%

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

収率 93.7%

溶媒

DMF

反応条件

後処理

1. 1
   ろ過The reaction mixture was filtered through Celite®
2. 2
   workup.ADDITIONthen diluted with DCM and water
3. 3
   その他The organic phase was dried
4. 4
   濃縮concentrated in vacuo
5. 5
   その他purified by chromatography

実験手順

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.

出典