Réaction #70002

Équation de réaction

Linoleoyl chloride

(E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid tert-butyl ester

EtOAc

→

(E)-Octadeca-9,12-dienoic acid 3-adamantan-1-yl-4′-(2-tert-butoxycarbonylvinyl)biphenyl-4-yl ester

Rendement 65.0%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   Lavagethe organic phase was washed twice with 1N HCl, water
2. 2
   Séchagedried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Autreremoved under reduced pressure

Mode opératoire

Linoleoyl chloride (208 mg, 0.696 mmol) was added to a solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid tert-butyl ester (200 mg, 0.464 mmol) in pyridine (2.2 ml). The resulting mixture was heated to 50° C. for 1 h, and then stirred at RT overnight. After addition of EtOAc, the organic phase was washed twice with 1N HCl, water, dried over Na2SO4, filtered and removed under reduced pressure. (E)-Octadeca-9,12-dienoic acid 3-adamantan-1-yl-4′-(2-tert-butoxycarbonylvinyl)biphenyl-4-yl ester was obtained as a colourless oil after purification on silica gel (EtOAc/hexane 5:95) in 65% yield (210 mg).

Source