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3,4-dihydro-2H-pyran → 5-Bromo-8-[(tetrahydro-2H-pyran-2-yloxy)methyl]quinoline

HRID 1849998
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HRID 1849998 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>C(Cl)Cl.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2
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참가 물질

6

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 72183353(5-Bromoquinolin-8-yl)methanol

생성물 1

HCID 867151505-Bromo-8-[(tetrahydro-2H-pyran-2-yloxy)methyl]quinoline수율 128.4%

시약·촉매·용매 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)촉매HCID 962Water용매
HCID 6344
Dichloromethane
용매

실험 절차

To a solution of (5-bromoquinolin-8-yl)methanol (8.0 g, 33.6 mmol) in methylene chloride (120 mL) were added pyridinium p-toluenesulfonate (844 mg, 3.3 mmol) and 3,4-dihydro-2H-pyran (6.1 mL, 67.2 mmol) and stirred at RT for 16 h. The reaction mixture was diluted with water, extracted with methylene chloride, dried with magnesium sulfate and concentrated. Purification by MPLC (20% ethyl acetate in hexanes) afforded 13.9 g of the title compound as a colorless oil.

후처리

  1. extractionextracted with methylene chloride
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customPurification by MPLC (20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-eaac7f16032f41b59464a92439ee963d
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957051B2

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