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Methyl Acrylate → Methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)acrylate

HRID 33379
Notes
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Reaction equation

HRID 33379 reaction equation
F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C1(C(N)C2CCCCC2)CCCCC1.[CH3:33][O:34][C:35](=[O:38])[CH:36]=[CH2:37].FC(F)(F)S(O[C:45]1[C:50]([N+:51]([O-:53])=[O:52])=[CH:49][C:48]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[CH:47][C:46]=1[C:62](=[O:64])[CH3:63])(=O)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)C>[C:62]([C:46]1[CH:47]=[C:48]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:49]=[C:50]([N+:51]([O-:53])=[O:52])[C:45]=1[CH:37]=[CH:36][C:35]([O:34][CH3:33])=[O:38])(=[O:64])[CH3:63]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 7294Methyl AcrylateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 210728242-Acetyl-4-benzyloxy-6-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 66751245Methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)acrylate

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

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.

Workup

  1. filtrationsuction filtered
  2. washwhile washing repeatedly with diethyl ether
  3. washThe combined organic phases are washed successively with 1 N hydrochloric acid, sodium carbonate solution and sodium chloride solution
  4. distillationThe solvent is distilled off
  5. customthe residue is crystallised from ethanol
  6. filtrationthe solid is filtered off
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-75969647c2494c0a89201f948e5b0b16
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429583B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes