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

HRID 15037

反応式

HRID 15037 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 866148912-Bromo-5-(2-tetrahydropyranyloxy)pyridine収率 55%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-22d50e01a3bc4b4d88cece5f10779ccd
出典データセット
uspto-grants-2010_06
特許番号
US07732456B2

関連ノート

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