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

HRID 53102

反応式

HRID 53102 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8c49cff7cbf7475b91c83a8130eef599
出典データセット
uspto-grants-1997_04
特許番号
US05618793

関連ノート

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