Methyl iodide → 5-bromo-2-(methoxymethyl)Pyridine

HRID 885942ノート

反応式

HRID 885942 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[H-].[Na+].I[CH3:13]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][CH3:13])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5200169(5-Bromopyridin-2-yl)methanol

生成物 1

HCID 540443575-bromo-2-(methoxymethyl)Pyridine収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 5-bromo-2-(hydroxymethyl)pyridine (150 mg, 0.798 mmol) in THF (8 mL) under nitrogen at r.t. was added sodium hydride (60% dispersion in oil, 64 mg, 1.60 mmol). After 30 minutes iodomethane was added and the reaction mixture was heated to 60° C. for 3 h, then cooled to r.t. and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo to give the title compound (70 mg, 65%) as 70% pure material. LCMS (ES+) 202.0 (M+H)+, RT 2.40 minutes (Method 1).

後処理

  1. temperaturecooled to r.t.
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between DCM (50 mL) and water (50 mL)
  4. washthe organic fraction was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-86074e2e6c134105a9677cb87d9ca856
出典データセット
uspto-grants-2012_08
特許番号
US08242116B2

反応ノート

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