Methyl Acrylate → 3-[3-(5-Phenyl-benzoxazol-2-yl)-phenyl]-acrylic acid methyl ester

HRID 659112

反応式

HRID 659112 の反応式
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C.Br[C:37]1[CH:38]=[C:39]([C:43]2[O:44][C:45]3[CH:51]=[CH:50][C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[CH:48][C:46]=3[N:47]=2)[CH:40]=[CH:41][CH:42]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:28][O:27][C:23](=[O:26])[CH:24]=[CH:25][C:41]1[CH:42]=[CH:37][CH:38]=[C:39]([C:43]2[O:44][C:45]3[CH:51]=[CH:50][C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[CH:48][C:46]=3[N:47]=2)[CH:40]=1

参加物

7

反応物 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 593348442-(3-Bromo-phenyl)-5-phenyl-benzoxazole

生成物 1

HCID 684169753-[3-(5-Phenyl-benzoxazol-2-yl)-phenyl]-acrylic acid methyl ester

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

実験手順

Tri(o-toly)phosphine (9 mg, 0.030 mmol), palladium(II) acetate (6 mg, 0.027 mmol), methyl acrylate (31 mg, 0.34 mmol), triethylamine (116 mg, 1.14 mmol) and aryl bromide (32) (100 mg, 0.29 mmol) in acetonitrile (3 mL) were heated in a CEM Discover microwave for 90 minutes at 90° C. The solvent was removed under a stream of nitrogen gas, water was added and the organics extracted with EtOAc. The organic layer was dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 20% EtOAc in heptane. Yield: 41 mg, 40%; LC-MS tr 1.86 min; HPLC Purity: 67%; MS (ES+) m/z 356 (M+H)

後処理

  1. customThe solvent was removed under a stream of nitrogen gas, water
  2. additionwas added
  3. extractionthe organics extracted with EtOAc
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationthe solvent concentrated in vacuo
  6. customThe crude product was purified by column chromatography
  7. washeluting with 20% EtOAc in heptane

出典と根拠

ORDレコード
ord-21798cf6470c46bf8402031b875a3969
出典データセット
uspto-grants-2011_12
特許番号
US08080567B2

関連ノート

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