Ethanol → 2-Benzyloxy-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

HRID 269537

반응식

HRID 269537 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2Br)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 587309812'-Bromobiphenyl-3-carboxylic acid ethyl ester

생성물 1

HCID 587309952-Benzyloxy-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester수율 41%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

2′-Bromobiphenyl-3-carboxylic acid ethyl ester (153 mg, 0.5 mmol) and 2-benzyloxyphenylboronic acid (125 mg (0.55 mmol) were dissolved in 1:1 toluene:ethanol (5 ml) under nitrogen. Potassium carbonate (552 mg, 4 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) were added and the mixture heated at 90° C. for 3 h. After cooling, the solvent was evaporated. The residue was partitioned between diethyl ether and water and the organic phase washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was flash chromatographed (silica gel, 2-10% EtOAc-isohexane) to give the title compound as a clear oil (84 mg, 41%). LC/MS Rt=4.09 [(M−OEt)H+]=363.1.

후처리

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between diethyl ether and water
  4. washthe organic phase washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customchromatographed (silica gel, 2-10% EtOAc-isohexane)

출처 및 근거

ORD 기록
ord-3b5e8a42ac9e4fa988a54bd09ce21266
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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