Ammonium Chloride → (2,6-Difluoropyridin-4-yl)methanol

HRID 426300ノート

反応式

HRID 426300 の反応式
C([O:9][CH2:10][C:11]1[CH:16]=[C:15]([F:17])[N:14]=[C:13]([F:18])[CH:12]=1)(=O)C1C=CC=CC=1.C[O-].[Na+].[Cl-].[NH4+]>CO>[F:18][C:13]1[CH:12]=[C:11]([CH2:10][OH:9])[CH:16]=[C:15]([F:17])[N:14]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 59184643(2,6-Difluoropyridin-4-yl)methyl benzoate

生成物 1

HCID 59184676(2,6-Difluoropyridin-4-yl)methanol収率 98.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of (2,6-difluoropyridin-4-yl)methyl benzoate (10.29 g, 41.325 mmol) in anhydrous methanol (80 mL) at room temperature, was added sodium methoxide (2.23 g, 41.325 mmol). After stirring for 20 min., excess ammonium chloride was added to the reaction mixture and stirring was continued for 30 min. The mixture was then evaporated in vacuo and the residue was dissolved in methanol-MC (1:9), filtered, and the filtrate was evaporated in vacuo to give a crude product. The crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:2 to 2:1)) to afford 5.9 g (98%) of (2,6-difluoropyridin-4-yl)methanol as a white solid. m.p. 66-67° C. 1H NMR (200 MHz, CDCl3) δ 2.19 (1H, t, J=5.8 Hz), 4.81 (2H, d, J=5.8 Hz), 6.84 (2H, s).

後処理

  1. stirringstirring
  2. waitwas continued for 30 min
  3. customThe mixture was then evaporated in vacuo
  4. dissolutionthe residue was dissolved in methanol-MC (1:9)
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customto give a crude product
  8. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:2 to 2:1))

出典と根拠

ORDレコード
ord-8a7aa6e4bb15441f82864dac349c7033
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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