Ethyl 2-ethylnicotinate → (2-Ethylpyridin-3-yl)methanol

HRID 630213ノート

反応式

HRID 630213 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:8]>C1COCC1>[CH2:7]([C:9]1[C:14]([CH2:15][OH:16])=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:8]

参加物

4

反応物 2

HCID 14580149Ethyl 2-ethylnicotinateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19690951(2-Ethylpyridin-3-yl)methanol収率 84.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a 0° C. mixture of lithium aluminum hydride (2.0 g, 53 mmol) in anhydrous THF (100 mL) was slowly added a solution of ethyl 2-ethylpyridine-3-carboxylate (4.8 g, 26.8 mmol) in anhydrous THF (30 mL). The reaction mixture was stirred at 0° C. for 1.5 hours. The reaction was quenched with 5 N NaOH. Water (200 mL) and EtOAc (200 mL) were added. The mixture was stirred for 30 minutes. The solid material was removed by filtration. The organic layer was recovered. The aqueous layer was extracted with EtOAc (2×100 mL). The combined organic extracts were dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (2-ethylpyridin-3-yl)methanol (3.1 g, 84% yield), which was used without further purification.

後処理

  1. customThe reaction was quenched with 5 N NaOH
  2. additionWater (200 mL) and EtOAc (200 mL) were added
  3. stirringThe mixture was stirred for 30 minutes
  4. customThe solid material was removed by filtration
  5. customThe organic layer was recovered
  6. extractionThe aqueous layer was extracted with EtOAc (2×100 mL)
  7. dry with materialThe combined organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-911928f423544f029e3331f9bc870531
出典データセット
uspto-grants-2016_04
特許番号
US09315521B2

反応ノート

読み込み中…