Reaction #61657

Reaction equation

tri-tert-butylphosphonium tetrafluoroborate

dicyclohexylmethylamine

methylacrylate

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

→

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

Solvents

dioxane

diethyl ether

Conditions

Workup

1. 1
   Filtrationsuction filtered
2. 2
   Washwhile washing repeatedly with diethyl ether
3. 3
   WashThe 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
   Otherthe residue is crystallised from ethanol
6. 6
   Filtrationthe solid is filtered off
7. 7
   Washwashed with ethanol

Procedure

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.

Source