Реакция #216845

Уравнение реакции

water

3-(1-adamantyl)-4-methoxybenzoyl chloride

allyl 2-fluoro-4-hydroxybenzoate

triethylamine

→

ester

Выход 78.1%

allyl 4-[3-(1-adamantyl)-4-methoxybenzoyloxy-]2-fluorobenzoate

Выход 78.1%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl ether
2. 2
   ДругоеThe organic phase is decanted
3. 3
   Промывкаwashed with water
4. 4
   Другоеdried on magnesium sulfate
5. 5
   Другоеevaporated
6. 6
   ДругоеThe resulting residue is purified by chromatography on a silica column
7. 7
   Промывкаeluted by a 50:50 mixture of dichloromethane and hexane

Методика

To a mixture of 1.96 g (10 mmoles) of allyl 2-fluoro-4-hydroxybenzoate, 1.53 ml (11 mmoles) of triethylamine and 25 ml of THF, there is slowly added a solution of 3 g (10 mmoles) of 3-(1-adamantyl)-4-methoxybenzoyl chloride in 50 ml of THF. The reaction medium is stirred at ambient temperature for 12 hours and then poured into water and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column, eluted by a 50:50 mixture of dichloromethane and hexane. After evaporation of the solvents, 3.63 g (78% yield) of the expected ester having a melting point of 102°-104° C. are obtained.

Источник