Reaktion #70000

Reaktionsgleichung

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

N-chloromethylphthalimide

K2CO3

NaI

→

3-[3′-Adamantan-1-yl-4′-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethoxy)-biphenyl-4-yl]acrylic acid tert-butyl ester

Ausbeute 55.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   WaschenThe organic phase was washed with water
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated under reduced pressure

Vorschrift

A solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester (200 mg, 0.464 mmol), N-chloromethylphthalimide (91 mg, 0.464 mmol), K2CO3 (70 mg, 0.464 mmol) and NaI (70 mg, 0.464 mmol) was stirred overnight at RT in the dark. The solvent was evaporated and the residue was taken up in EtOAc. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. 3-[3′-Adamantan-1-yl-4′-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethoxy)-biphenyl-4-yl]acrylic acid tert-butyl ester was obtained after purification on silica gel (EtOAc/hexane 15:85) in 55% yield (150 mg).

Quelle