Borane;tetrahydrofuran → Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate

HRID 2098955ノート

反応式

HRID 2098955 の反応式
[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.B.C1COCC1>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 574675964-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-3-((methyloxy)carbonyl)benzoic acid

生成物 1

HCID 57467597Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate収率 105.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
23 °C

実験手順

To a stirred solution of 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(methoxycarbonyl)benzoic acid T37.2 (0.416 g, 1 mmol) in THF (14 mL) at 0° C. was added borane-THF (3 mL, 3 mmol, 1.0M). The reaction was warmed to 23° C. and stirred for 46 hours. The reaction was then concentrated in vacuo. The reaction was diluted with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield T37.3 as a colorless solid (0.307 g, 77% yield).

後処理

  1. concentrationThe reaction was then concentrated in vacuo
  2. additionThe reaction was diluted with 1N HCl
  3. extractionextracted three times with EtOAc
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure
  7. customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-740c0c42973f45e4963bc04053215a52
出典データセット
uspto-grants-2013_05
特許番号
US08450522B2

反応ノート

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