4-Methoxybenzyl alcohol → 3-Benzyloxy-6-iodo-2-(4-methoxybenzyloxy)pyridine

HRID 625967

反応式

HRID 625967 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.[H-].[Na+].[H][H].[CH2:15]([O:22][C:23]1[C:24](Br)=[N:25][C:26]([I:29])=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.O>[CH2:15]([O:22][C:23]1[C:24]([O:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:25][C:26]([I:29])=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 110255633-(Benzyloxy)-2-bromo-6-iodopyridineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 866754893-Benzyloxy-6-iodo-2-(4-methoxybenzyloxy)pyridine収率 81.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a 0° C. solution of p-methoxybenzyl alcohol (13.83 g, 100 mmol) in 33 mL DMF was added sodium hydride (4 g, 100 mmol) slowly. The mixture was stirred at room temperature until evolution of hydrogen had ceased, and crude 3-(benzyloxy)-2-bromo-6-iodopyridine (13.01 g, 33.4 mmol) was added. The resulting solution was heated to 100° C. for 1 h under nitrogen. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The aqueous layer was removed and discarded. The organic layer was collected, dried over anhydrous magnesium sulfate and purified by silica gel chromatography to afford 3-(benzyloxy)-6-iodo-2-[(4-methoxybenzyl)oxy]pyridine (12.1 g, 27.1 mmol, 81% yield). ES-MS (M+H)+=448.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe aqueous layer was removed
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-f9eb8841c74a40c78695c720eed21e84
出典データセット
uspto-grants-2016_04
特許番号
US09309199B2

関連ノート

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