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

HRID 1789760노트

반응식

HRID 1789760 반응식
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]

참가 물질

4

반응물 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 17946394HCID 17946394, 화합물

생성물 1

HCID 115138722-(2-ETHOXYPYRIDIN-3-YLOXY)ETHANOL수율 41%

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31743a51b6504dc4aba84a0f0347480d
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071180B2

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