Réaction #69998

Équation de réaction

3-adamantan-1-yl-4′-bromo-biphenyl-4-ol

tert-butyl acrylate

NEt3

NMP

→

desired compound

Rendement 93.2%

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

Rendement 93.2%

Solvants

DCM

dioxane

H2O

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONcontaining
2. 2
   Températurecooled condenser
3. 3
   Autrewas immerged in a pre-heated oil bath
4. 4
   Autreto return to RT
5. 5
   Lavagewashed with H2O
6. 6
   SéchageThe organic phase was dried over Na2SO4
7. 7
   Autrethe solvent was removed under reduced pressure
8. 8
   AutreThe crude reaction mixture
9. 9
   AutreThe suspension was then sonicated for 20 min
10. 10
    workup.STIRRINGstirred overnight
11. 11
    FiltrationAfter filtration of the latter

Mode opératoire

Pd(OAc)2 (6.7 mg, 0.03 mmol) was added into a flask containing a mixture of 3-adamantan-1-yl-4′-bromo-biphenyl-4-ol (1.15 g, 2.99 mmol), tert-butyl acrylate (1.75 g, 11.96 mmol), NEt3 (1.25 ml, 8.97 mmol), tetrabutylammonium chloride (1.329 g, 4.78 mmol) and NMP (3 ml). The flask, equipped with a glycol-cooled condenser, was immerged in a pre-heated oil bath (110° C.) and the reaction mixture was stirred at this temperature overnight. The mixture was allowed to return to RT and was diluted with DCM and washed with H2O. The organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure. The crude reaction mixture was taken-up in dioxane (10 ml) and the resulting solution added dropwise to 40 ml of H2O. The suspension was then sonicated for 20 min and stirred overnight. After filtration of the latter, 1.2 g (93% yield) of the desired compound as a grey solid was obtained.

Source