反应 #61657

反应方程式

tri-tert-butylphosphonium tetrafluoroborate

dicyclohexylmethylamine

methylacrylate

2-acetyl-4-benzyloxy-6-nitro-phenyl trifluoromethanesulphonate

→

methyl 3-(2-acetyl-4-benzyloxy-6-nitro-phenyl)-acrylate

溶剂

dioxane

diethyl ether

反应条件

后处理

1. 1
   过滤suction filtered
2. 2
   洗涤while washing repeatedly with diethyl ether
3. 3
   洗涤The combined organic phases are washed successively with 1 N hydrochloric acid, sodium carbonate solution and sodium chloride solution
4. 4
   workup.DISTILLATIONThe solvent is distilled off
5. 5
   其他the residue is crystallised from ethanol
6. 6
   过滤the solid is filtered off
7. 7
   洗涤washed with ethanol

实验过程

5.88 g (6.42 mmol) tris-(dibenzylideneacetone)-dipalladium, 3.50 g (12.01 mmol) tri-tert-butylphosphonium tetrafluoroborate, 81.2 mL (371 mmol) dicyclohexylmethylamine, 105.8 g (286 mmol) tetrabutylammonium iodide and 32.6 mL (362 mmol) methylacrylate are added to a solution of 100 g (238 mmol) 2-acetyl-4-benzyloxy-6-nitro-phenyl trifluoromethanesulphonate in 360 mL dioxane. The reaction mixture is stirred for 2 hours at 80° C. under a nitrogen atmosphere in the presence of 100 g molecular sieve 4A and then combined with 2 L diethyl ether and 500 g silica gel. After 10 minutes the silica gel is suction filtered, while washing repeatedly with diethyl ether. The combined organic phases are washed successively with 1 N hydrochloric acid, sodium carbonate solution and sodium chloride solution. The solvent is distilled off, the residue is crystallised from ethanol and the solid is filtered off and washed with ethanol.

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