反応 #1284178

反応方程式

methyl 11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

(3-dimethylaminopropyl)triphenylphosphonium bromide hydrobromide

n-butyl lithium hexane

→

desired product

Methyl 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度under ice-cooling
2. 2
   温度cooling for one hour
3. 3
   workup.ADDITIONTo the mixture is dropwise added under ice-
4. 4
   温度cooling a solution
5. 5
   その他obtained
6. 6
   workup.STIRRINGAfter stirring the mixture at room temperature for 2 hours
7. 7
   抽出the mixture is extracted with 800 ml of ethyl acetate
8. 8
   洗浄After washing the
9. 9
   抽出extract with saturated aqueous sodium chloride solution
10. 10
    その他drying the
11. 11
    抽出extract over anhydrous sodium sulfate
12. 12
    workup.DISTILLATIONthe solvent is distilled away under reduced pressure
13. 13
    その他The residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate:triethylamine=10:10:1)

実験手順

In this Example, 45 g of (3-dimethylaminopropyl)triphenylphosphonium bromide hydrobromide is suspended in 200 ml of tetrahydrofuran under a nitrogen atmosphere and 82 ml of 1.6N-n-butyl lithium hexane solution is added thereto under ice-cooling. The mixture is stirred under ice-cooling for one hour. To the mixture is dropwise added under ice-cooling a solution obtained by dissolving 10 g of methyl 11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate in 200 ml of tetrahydrofuran. After stirring the mixture at room temperature for 2 hours, the mixture is extracted with 800 ml of ethyl acetate. After washing the extract with saturated aqueous sodium chloride solution and drying the extract over anhydrous sodium sulfate, the solvent is distilled away under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate:triethylamine=10:10:1) to obtain 2.0 g of trans form and 5.6 g of cis form of the desired product.

出典