反応 #70002

反応方程式

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

収率 65.0%

溶媒

pyridine

反応条件

後処理

1. 1
   洗浄the organic phase was washed twice with 1N HCl, water
2. 2
   乾燥dried over Na2SO4
3. 3
   ろ過filtered
4. 4
   その他removed under reduced pressure

実験手順

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).

出典