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

HRID 33379

反応式

HRID 33379 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 67553Tetrabutylammonium Iodide触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-75969647c2494c0a89201f948e5b0b16
出典データセット
uspto-grants-2008_09
特許番号
US07429583B2

関連ノート

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