2-Butyl-6-chloro-4-Methylnicotinaldehyde synthesis

Yield:-

Steps:

Multi-step reaction with 6 steps
1: piperidine / ethanol / 3 h / Heating
2: 1 N aq. (NH₄)2Ce(NO₃)6 / acetone / 0.33 h / 0 °C
3: 73.7 percent / m-chloroperbenzoic acid / CHCl₃ / 4 h / Ambient temperature
4: 42.7 percent / POCl₃ / 2 h / Heating
5: 82.9 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C
6: 87.8 percent / MnO₂ / CHCl₃ / 5 h / Heating

References:

Ueyama;Yanagisawa;Kawai;Sonegawa;Baba;Mochizuki;Kosakai;Tomiyama [Chemical and Pharmaceutical Bulletin,1994,vol. 42,# 9,p. 1841 - 1849]