p-Toluenesulfonic acid → 2-Bromo-5-(2-tetrahydropyranyloxy)pyridine

HRID 15037

반응식

HRID 15037 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:9]2)=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 27628652-Bromo-5-hydroxypyridine

생성물 1

HCID 866148912-Bromo-5-(2-tetrahydropyranyloxy)pyridine수율 55%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-bromo-5-hydroxypyridine (1.0 g, 5.75 mmols), 3,4-dihydro-2H-pyran (0.80 mL, 8.77 mmols) and p-toluenesulfonic acid (110 mg, 0.578 mmol) was stirred overnight in dichloromethane (20 mL) at room temperature. The reaction liquid was diluted with chloroform, washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:20-1:10) to provide the title compound (0.81 g, 55%).

후처리

  1. customThe reaction liquid
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe resulting residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:20-1:10)

출처 및 근거

ORD 기록
ord-22d50e01a3bc4b4d88cece5f10779ccd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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