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

HRID 991690ノート

反応式

HRID 991690 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-c2b1a2f183cd438aa1aea5abf6171fde
出典データセット
uspto-grants-2002_10
特許番号
US06465467B1

反応ノート

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