(2E)-3-(5-methylthiophen-2-yl)-1-(3-nitrophenyl)prop-2-en-1-one synthesis

Yield:1440663-62-6 65%

Reaction Conditions:

with silver (II) carbonate;2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;lithium acetate;palladium diacetate;tricyclohexylphosphine in 1,2-dimethoxyethane at 100; for 24 h;Schlenk technique;Inert atmosphere;

Steps:

(E)-3-(5-methylthiophen-2-yl)-1-(3-nitrophenyl)prop-2-en-1-one

General procedure: In a glove box, a 25 mL of Schlenk tube equipped with a stir bar was charged with Pd(OAc)2 (0.03 mmol, 0.1 equiv), PCy3 (0.03 or 0.06 mmol, 0.1 or 0.2 equiv), LiOAc (0.45 mmol, 1.5 equiv) (or NaOAc), TEMPO (0.12 mmol, 0.4 equiv), Ag2CO3 (0.9 mmol, 3 equiv). The tube was fitted with a rubber septum and removed out of the glove box. DME (2 mL), propiophenone (0.9 mmol, 3.0 equiv) and thiophene (0.3 mmol, 1.0 equiv) were added in turn to the Schlenk tube through the rubber septum using syringes, and then the septum was replaced with a Teflon screwcap under nitrogen flow (if the thiophene or the substituted propiophenone was solid, it was added to the tube in the glove box). The reaction mixture was stirred at 100 oC or 120 oC for 24 h. After cooling down, the reaction mixture was diluted with 10 mL of ethyl ether, filtered through a pad of silica gel, followed by washing the pad of the silica gel with the same solvent (20 mL), concentrated under reduced pressure. The residue was then purified by flash chromatography on silica gel with 2-15 % ethyl ether in petroleum ether as eluent to provide the corresponding product.

References:

Shang, Yaping;Jie, Xiaoming;Zhou, Jun;Hu, Peng;Huang, Shijun;Su, Weiping [Angewandte Chemie - International Edition,2013,vol. 52,# 4,p. 1299 - 1303][Angew. Chem.,2013,vol. 125,# 4,p. 1337 - 1341,5] Location in patent:supporting information