Dimethylformamide → 2-Hydroxy-4-morpholin-4-yl-benzaldehyde

HRID 349673

反応式

HRID 349673 の反応式
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[N:11]1([C:17]2[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])(=O)C.[Na+]>O>[OH:23][C:19]1[CH:18]=[C:17]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:22]=[CH:21][C:20]=1[CH:4]=[O:5]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 1413433-MorpholinophenolHCID 517045Sodium Acetate

生成物 1

HCID 98156592-Hydroxy-4-morpholin-4-yl-benzaldehyde収率 23%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

DMF (10 mL) was treated dropwise with phosphorus oxychloride (2.3 g, 15 mmol). The reaction was kept at 25° C. by cooling on ice. The reaction mixture was treated with 3-(4-morpholinyl)phenol (2.5 g, 14 mmol) in small portions, stirred for 30 min at room temperature, then stirred at 100° C. for 8 h. After cooling, the mixture was poured into aqueous sodium acetate (1 M, 40 mL) and 10 mL of water was added. The resulting precipitate was collected by filtration, washed with water (10 mL), air dried, and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 CHCl3/ether) to yield the product as a light gray solid (0.66 g, 23%). See U.S. Pat. No. 4,147,552.

後処理

  1. customwas kept at 25° C.
  2. temperatureby cooling on ice
  3. stirringstirred at 100° C. for 8 h
  4. temperatureAfter cooling
  5. additionwas added
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water (10 mL), air
  8. customdried
  9. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 CHCl3/ether)

出典と根拠

ORDレコード
ord-0d94bf92443c410c9049b939710b8591
出典データセット
uspto-grants-2007_02
特許番号
US07179912B2

関連ノート

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