反応 #65708

反応方程式

4-(2-morpholinoethoxy)benzaldehyde

n-butyllithium

[1-(2,2-dimethyl-1,3-benzodithiol-5-yl)ethyl]triphenylphosphonium bromide

→

4-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine

収率 35.2%

溶媒

tetrahydrofuran

hexane

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONThe mixture was then poured on to ice
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄The combined extracts were washed with water
4. 4
   その他dried
5. 5
   その他evaporated
6. 6
   洗浄After chromatography (silica gel, eluting agent ethyl acetate) and crystallization from ether/hexane

実験手順

6.6 g of [1-(2,2-dimethyl-1,3-benzodithiol-5-yl)ethyl]triphenylphosphonium bromide were dissolved in 40 ml of tetrahydrofuran and treated slowly at 0° C. with 9 ml of a 1.5 molar solution of n-butyllithium in hexane. After 40 minutes, 3.5 g of 4-(2-morpholinoethoxy)benzaldehyde in 10 ml of tetrahydrofuran were added dropwise to the dark red solution and the mixture was stirred at 20° C. for 16 hours. The mixture was then poured on to ice and extracted with ethyl acetate. The combined extracts were washed with water, dried and evaporated. After chromatography (silica gel, eluting agent ethyl acetate) and crystallization from ether/hexane, there were obtained 1.8 g of 4-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine in the form of colorless crystals, melting point 90°-91° C.

出典