Реакция #418003

Уравнение реакции

3,3-diethoxy-propene

EtOAc

1-ethoxy-4-((4-iodophenyl)ethynyl)benzene

3,3-diethoxy-propene

tributylamine

→

desired product

3-[4-(4-Ethoxy-phenylethynyl)-phenyl]-propionic acid ethyl ester

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture is stirred at 120° C. for 5 d
2. 2
   ТемператураAfter cooling
3. 3
   Промывкаthe mixture is washed with 1N potassium hydrogensulfate solution and water
4. 4
   СушкаThe organic layer is dried over sodium sulphate
5. 5
   Другоеthe solvent is evaporated
6. 6
   ДругоеThe residue is purified by column chromatography (silica gel; PE:DCM 1:1)

Методика

To 1.80 g (5.17 mmol) 1-ethoxy-4-((4-iodophenyl)ethynyl)benzene (XII.1) in 24 mL DMF are added 2.36 mL (15.5 mmol) 3,3-diethoxy-propene, 3.69 mL (15.5 mmol) tributylamine, 1.44 g (5.17 mmol) tetrabutylammoniumchloride and 0.04 g (0.16 mmol) palladium(II)acetate under argon. The mixture is stirred at 120° C. for 12 h. After that time, 1.18 mL (7.76 mmol) 3,3-diethoxy-propene are added and the mixture is stirred at 120° C. for 5 d. After cooling, EtOAc is added and the mixture is washed with 1N potassium hydrogensulfate solution and water. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; PE:DCM 1:1) to yield the desired product.

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