Water → 5-[(2-Methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde

HRID 53102

반응식

HRID 53102 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=1.[H-].[Na+].O>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 2783895-Hydroxy-2-pyridinecarboxaldehyde

생성물 1

HCID 199615215-[(2-Methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

Methoxyethoxymethyl chloride (MEM) (19 g, 153 mmol) was added to a solution of 5-hydroxy-2-pyridinecarboxaldehyde (18.4 g, 149 mmol) in 300 ml DMF. NaH (6.3 g of 60% oil dispersion, 158 mmol) were added in portions while cooling the mixture to maintain 20°-30° C. The mixture was stirred an additional 1 hour at 25° C. 5 ml water were added, most of the solvent was evaporated, and water was added to the residue. The mixture was extracted with EtOAc. The extracts were dried over Na2SO4, filtered, and evaporated to a residue. The residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65) to obtain 5-[(2-methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde: C10H13NO4 (211.22); 1H-NMR (CDCl3) δ10.01 (s,1), 8.52 (d,1), 7.93 (d,1), 7.49 (m,1), 5.39 (s,2), 3.80 (m,2), 3.53 (m,2), 3.32 (s,3).

후처리

  1. temperaturewhile cooling the mixture
  2. temperatureto maintain 20°-30° C
  3. customwas evaporated
  4. additionwater was added to the residue
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialThe extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to a residue
  9. customThe residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

출처 및 근거

ORD 기록
ord-8c49cff7cbf7475b91c83a8130eef599
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618793

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