反応 #58729

反応方程式

6-methyl nicotinic acid methyl ester

iodine

2-iodo-2-methylpropane

trifluoroacetic acid

NaHCO3

Na2S2O3

→

title compound

収率 46.3%

6-Formyl-nicotinic acid methyl ester

収率 46.3%

溶媒

DMSO

反応条件

後処理

1. 1
   抽出The reaction mixture was extracted with ethyl acetate (3×100 mL)
2. 2
   乾燥The combined organic phases were dried over anhydrous Na2SO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated

実験手順

A solution of 6-methyl nicotinic acid methyl ester (1.00 g, 6.62 mmol), iodine (1.68 g, 6.62 mmol), 2-iodo-2-methylpropane (0.478.g, 2.60 mmol) and trifluoroacetic acid (2.26 g, 19.8 mmol) in anhydrous DMSO was heated for 3 h at 160° C. The reaction mixture was cooled to room temperature (rt) and treated with 1 N aq. Na2S2O3 (50 mL). The reaction mixture was adjusted to pH 10 with 1 N aq. NaHCO3. The reaction mixture was extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated. Chromatography of the residue (SiO2; 0-3% EtOH:DCM) gave the title compound as a solid (0.506 g, 46%).

出典