Dimethylformamide → 3-Bromo-5-(methoxymethyl)pyridine

HRID 340472ノート

反応式

HRID 340472 の反応式
[H-].[Na+].[CH3:3]N(C=O)C.[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][OH:16])[CH:12]=[N:13][CH:14]=1.CI>O>[Br:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]([CH2:15][O:16][CH3:3])[CH:10]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2784733(5-Bromo-3-pyridinyl)methanol

生成物 1

HCID 186245693-Bromo-5-(methoxymethyl)pyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Sodium hydride (61% in oil) (11 mg) was added to a DMF (0.9 ml) solution containing (5-bromopyridin-3-yl)methanol (34 mg) under ice cooling, followed by stirring for 1 hour. Then, methyl iodide (17 μl) was added, followed by stirring at room temperature for 13 hours. Thereafter, water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 1:1), and a light yellow solid of 3-bromo-5-(methoxymethyl)pyridine (26.5 mg) was thus obtained.

後処理

  1. stirringby stirring at room temperature for 13 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationSubsequently, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 1:1)

出典と根拠

ORDレコード
ord-eed2cc3d6dfb422cbb630b89fb5ffbf3
出典データセット
uspto-grants-2014_11
特許番号
US08895585B2

反応ノート

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