Reaktion #216845

Reaktionsgleichung

water

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

allyl 2-fluoro-4-hydroxybenzoate

triethylamine

→

ester

Ausbeute 78.1%

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

Ausbeute 78.1%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl ether
2. 2
   SonstigeThe organic phase is decanted
3. 3
   Waschenwashed with water
4. 4
   Sonstigedried on magnesium sulfate
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe resulting residue is purified by chromatography on a silica column
7. 7
   Wascheneluted by a 50:50 mixture of dichloromethane and hexane

Vorschrift

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.

Quelle