Réaction #1121720

Équation de réaction

triethylamine

4-methoxybenzoyl chloride

1,3-dimethyl-2-imidazolidinone

4-tert-butylacetophenone

→

uncolored oil

Rendement 7.0%

1-(4-Tert-butylphenyl)-vinyl 4-methoxybenzoate

Rendement 7.0%

Solvants

hexane ethyl acetate

chloroform

Conditions de réaction

Traitement

1. 1
   AutreThe first collected fraction was purified twice by flash chromatography (hexane/dichloromethane 3:2 and next, hexane/dichloromethane 4:1)

Mode opératoire

4-methoxybenzoyl chloride (2.35 g, 13.8 mmol), 0.65 g of cuprous chloride and 5.6 mL of 1,3-dimethyl-2-imidazolidinone were added to crude 4-tert-butylacetophenone trimethylsilylenol (6.7 mmol). After stirring the solution for 20 hours at room temperature, 1.4 mL of triethylamine and 10 mL of chloroform were added. Then the solution was chromatographied through flash silica column (hexane/ethyl acetate 10:1). The first collected fraction was purified twice by flash chromatography (hexane/dichloromethane 3:2 and next, hexane/dichloromethane 4:1) giving 0.14 g of an uncolored oil corresponding to 1-(4-tert-butylphenyl)-vinyl 4-methoxybenzoate. Yield 7%.

Source