반응 #61657

반응 방정식

tri-tert-butylphosphonium tetrafluoroborate

dicyclohexylmethylamine

methylacrylate

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

→

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

용매

dioxane

diethyl ether

반응 조건

후처리

1. 1
   여과suction filtered
2. 2
   세척while washing repeatedly with diethyl ether
3. 3
   세척The 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
   기타the residue is crystallised from ethanol
6. 6
   여과the solid is filtered off
7. 7
   세척washed with ethanol

실험 절차

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.

출처