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

HRID 349673

반응식

HRID 349673 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 98156592-Hydroxy-4-morpholin-4-yl-benzaldehyde수율 23%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0d94bf92443c410c9049b939710b8591
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179912B2

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