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3-Bromo-3-buten-1-ol → γ-Methylene-6-quinolinepropanol

HRID 1257885
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인쇄 미리보기

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HRID 1257885 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)O1.Br[C:21](=[CH2:25])[CH2:22][CH2:23][OH:24].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:21](=[CH2:25])[CH2:22][CH2:23][OH:24])=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=1
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참가 물질

8

반응물 3

HCID 5339753-Bromo-3-buten-1-olHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 162177846-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

생성물 1

HCID 67224309γ-Methylene-6-quinolinepropanol

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매
HCID 962
Water
용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

Palladium acetate (100 mg, 0.6 mmol) was added to a solution of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (8.0 g, 31 mmol) and 3-bromo-3-buten-1-ol (6.2 g, 41 mmol) in toluene (118 mL) and water (12 mL) followed by addition of 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (500 mg, 1 mmol). The mixture was stirred at 100° C. for 6 h. After cooling to RT, the mixture was diluted with EtOAc, washed with water and brine. The organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with EtOAc in methylene chloride (0-50%) to afford the desired product.

후처리

  1. temperatureAfter cooling to RT
  2. washwashed with water and brine
  3. dry with materialThe organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel with EtOAc in methylene chloride (0-50%)

출처 및 근거

ORD 기록
ord-a07c6f2c8c254e21af3c0fbc3be368fc
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461330B2

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