Ammonium Chloride → (2,3,6-Trifluoropyridin-4-yl)methanol

HRID 426228ノート

反応式

HRID 426228 の反応式
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][O:10]C(=O)C2C=CC=CC=2)[CH:5]=[C:4]([F:19])[N:3]=1.C[O-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][OH:10])[CH:5]=[C:4]([F:19])[N:3]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 59184767Benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester

生成物 1

HCID 22392087(2,3,6-Trifluoropyridin-4-yl)methanol収率 95.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester (3.43 g, 12.8 mmol) in anhydrous methanol (50 ml) at room temperature, was added sodium methoxide (693 mg, 12.8 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-dichloromethane (1:9), filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:4) to EA) to afford 2.0 g (95%) of (2,3,6-trifluoro-pyridin-4-yl)-methanol as a white solid. m.p. 48-49° C.; 1H NMR (200 MHz, CDCl3) δ 2.18 (1H, t, J=5.6 Hz), 4.88 (2H, d, J=5.6 Hz), 7.02 (1H, 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-dichloromethane (1:9)
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent, EA:hexane (1:4) to EA)

出典と根拠

ORDレコード
ord-8486a0e3c9164bed8c604a90d8e44457
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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