Ethanol → 2-(2-ETHOXYPYRIDIN-3-YLOXY)ETHANOL

HRID 493346ノート

反応式

HRID 493346 の反応式
Br[C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][Si](C(C)(C)C)(C)C)=[CH:6][CH:5]=[CH:4][N:3]=1.[O-:19][CH2:20][CH3:21].[Na+].CCO>>[CH2:20]([O:19][C:2]1[C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:21]

参加物

4

反応物 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 17946394HCID 17946394、化合物

生成物 1

HCID 115138722-(2-ETHOXYPYRIDIN-3-YLOXY)ETHANOL収率 41%

反応条件

温度
70 °C

実験手順

The product obtained in Step 1 above (13.2 g, 39.7 mmol) was added to sodium ethoxide in EtOH [prepared from Na (10.5 g, 457 mmol) and EtOH (200 mL)]. The resulting mixture was heated at 70° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with ice water (0.8 L) and extracted with EtOAc (×4). The combined organic phases were washed twice with brine, dried (MgSO4) and concentrated. The resulting dark red oil was purified by column chromatography on silica using toluene/Et3N (95:5), followed by (90:10), as eluent to give 3.0 g (41%) of the title product as a red oil. HRMS m/z calcd for C9H13NO3 (M)+ 183.0896. Found: 183.0895.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with EtOAc (×4)
  3. washThe combined organic phases were washed twice with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting dark red oil was purified by column chromatography on silica

出典と根拠

ORDレコード
ord-7356ae6e618c450a908dacbeb028d583
出典データセット
uspto-grants-2009_05
特許番号
US07534794B2

反応ノート

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