2-吡啶甲酸加热脱羧后对羰基化物进行亲核加成得到2-吡啶甲醇的反应。此反应以英国化学家Dalziel Hammick的名字命名。反应以对异丙基甲苯作为溶剂可以提高反应产率【 J. Am. Chem. Soc. 71 (3): 887. doi:10.1021/ja01171a034】。

利用2-吡啶甲酸硅酯作为底物可以提高反应产率。

【Effenberger F, Tetrahedron, 1988, 44, 3281】

反应机理

中间体2被称为Hammick中间体，其对醛酮进行亲核加成得到产物。

反应实例

Phenyl 2-pyridyl carbinol (6). Picolinic acid 7 (5 g) was dissolved in freshly distilled PhCHO 4 (30 g) and stirred at 140 C for 75 min. To this were added HCl and ether to afford a brown oil (5 mL). The mixture was washed with water and dried over anhyd sodium sulphate. In vacuo distillation afforded colourless liquid 6 (3 mL), bp 181–183 C/16 mm, which solidified on standing and after two crystallizations from ligroin (bp 80–100 C) and one from ligroin–PhH (1:1) had mp 78 C

【Hammick DLL, J Chem Soc., 1939, 809】

【Effenberger F, Tetrahedron, 1988, 44, 3281】

相关文献

1 Hammick DLL J Chem Soc 1939 809

2 Hammick DLL J Chem Soc 1949 173, 659

3R Brown BR Quat Rev 1951 5

4 Hammick DLL J Chem Soc 1953 3825

5 Effenberger F Tetrahedron 1988 44 3281

6 Vorbru¨gen H Heterocycles 1994 37 1731

7 Schmidt A Lett Org Chem 2005 2 37