Acetic Acid → 1-(Pyridin-4-yl)butane-1,3-dione

HRID 326970

반응식

HRID 326970 반응식
[C:1]([O:9]C)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C[O-].[Na+].[CH3:14][C:15]([CH3:17])=[O:16].C(O)(=O)C>C(OCC)C>[O:9]=[C:1]([C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1)[CH2:14][C:15](=[O:16])[CH3:17]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 180AcetoneHCID 227085Methyl isonicotinateHCID 10942334Sodium Methoxide

생성물 1

HCID 124183301-(Pyridin-4-yl)butane-1,3-dione

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a suspension of methyl isonicotinate (96.0 g, 0.7 mol) and sodium methoxide (45.4 g, 0.84 mol) in ethyl ether (1 l), acetone (81.3 g, 1.4 mol) was added dropwise at 25°~30° C. and stirring was continued for 2 hrs. under reflux. After cooling, acetic acid (50.4 g, 0.84 mol) was added to the reaction mixture, the organic layer was separated, washed twice with H2O, dried over anhydrous MgSO4 and evaporated. The residue (87.5 g) was distilled under reduced pressure to give the title compound as a pale yellow oil which solidified in the refrigerator; yield: 40.2 g; bp 135°~138° C./10 mmHg; mp 62°~64.5° C. (Lit. bp 118°~120° C.; mp 66.5°~67° C.; R. Levine, J. K. Sneed, J. Am. Chem. Soc., 73, 5614 (1951).). ##STR30##

후처리

  1. additionwas added dropwise at 25°~30° C.
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. washwashed twice with H2O
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated
  8. distillationThe residue (87.5 g) was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-bffd8543561940169d39de551465e1f7
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272036

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