Reaction #1121720

Reaction equation

triethylamine

4-methoxybenzoyl chloride

1,3-dimethyl-2-imidazolidinone

4-tert-butylacetophenone

→

uncolored oil

Yield 7.0%

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

Yield 7.0%

Solvents

hexane ethyl acetate

chloroform

Conditions

Workup

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

Procedure

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