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Hydrochloric Acid → ({1-[(3-Hydroxyphenyl)ethynyl]-2-naphthyl}oxy)acetic acid

HRID 2390369
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HRID 2390369 반응식
C([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1Br)(C)(C)C.[OH:21][C:22]1[CH:23]=[C:24]([C:28]#[CH:29])[CH:25]=[CH:26][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCCCC1.Cl>O.CC(C)=O.C(Cl)Cl.O1CCOCC1.[Pd](Cl)Cl>[OH:21][C:22]1[CH:23]=[C:24]([C:28]#[C:29][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:18][C:9]=2[O:8][CH2:7][C:6]([OH:5])=[O:20])[CH:25]=[CH:26][CH:27]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

11

반응물 5

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 11776TriphenylphosphineHCID 139144m-EthynylphenolHCID 58522023tert-Butyl[(1-bromo-2-naphthyl)oxy]acetate2회

생성물 1

HCID 46865199({1-[(3-Hydroxyphenyl)ethynyl]-2-naphthyl}oxy)acetic acid

시약·촉매·용매 5

HCID 24290Palladium Chloride촉매HCID 180Acetone용매HCID 962Water용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

A mixture of (1-bromo-naphthalen-2-yloxy)-acetic acid tert-butyl ester (Intermediate 217, 125 mg; 0.37 mmol), 3-hydroxyphenylacetylene (53 mg; 0.44 mmol), palladium(II) chloride (3.3 mg; 0.02 mmol), triphenylphosphine (10 mg; 0.04 mmol) and piperidine (73 μl; 0.74 mmol) in distilled water (1.1 ml) and Acetone (1.4 ml) was stirred overnight at 60° C. The reaction mixture was extracted by EtOAc and the organic phases was dried over MgSO4, concentrated to dryness and purified by preparative HPLC. The intermediate obtained was diluted in DCM (1 ml) and treated with a 4 M solution of HCl in dioxane (930 μl). After stirring overnight, the reaction mixture was concentrated to dryness and purified by preparative HPLC to afford the title compound as a beige solid.

후처리

  1. extractionThe reaction mixture was extracted by EtOAc
  2. dry with materialthe organic phases was dried over MgSO4
  3. concentrationconcentrated to dryness
  4. custompurified by preparative HPLC
  5. customThe intermediate obtained
  6. stirringAfter stirring overnight
  7. concentrationthe reaction mixture was concentrated to dryness
  8. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-96953d28d6ea48d583122c2b837410c7
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273769B2

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