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

HRID 659112

반응식

HRID 659112 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-21798cf6470c46bf8402031b875a3969
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080567B2

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