反応 #485494

反応方程式

(5RS,9SR,10RS)-2-bromo-3-heptyloxy-10-hydroxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocycloheptene

2,6-lutidine

t-butyldimethylsilyl triflate

→

(5RS,9SR,10RS)-2-bromo-10-t-butyldimethylsilyloxy-3-heptyloxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocycloheptene

溶媒

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONpoured on to ice
2. 2
   抽出The mixture was extracted with diethyl ether
3. 3
   洗浄washed with 1N HCl and water
4. 4
   乾燥dried over Na2SO4
5. 5
   その他evaporated
6. 6
   ろ過Column filtration (SiO2/hexane)

実験手順

4.49 g of the thus-obtained (5RS,9SR,10RS)-2-bromo-3-heptyloxy-10-hydroxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocycloheptene were placed in 12 ml of CH2Cl2 under argon and treated with 2.58 ml of 2,6-lutidine followed by 3.08 ml of t-butyldimethylsilyl triflate. The mixture was stirred at 35° C. overnight and then poured on to ice. The mixture was extracted with diethyl ether, washed with 1N HCl and water, dried over Na2SO4 and evaporated. Column filtration (SiO2/hexane) gave 5.39 g of (5RS,9SR,10RS)-2-bromo-10-t-butyldimethylsilyloxy-3-heptyloxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocycloheptene as a colourless oil.

出典