3-Pyridinecarboxaldehyde → Ethyl 5-(pyridin-3-yl)-2,4-pentadienoate

HRID 478733노트

반응식

HRID 478733 반응식
[Li+].CC([N-]C(C)C)C.C(=O)=O.CO.C(OP([CH2:22]/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])(OCC)=O)C.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[N:33][CH:32]=1>C1COCC1.C(O)(=O)C>[N:33]1[CH:34]=[CH:35][CH:36]=[C:31]([CH:30]=[CH:22][CH:23]=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:32]=1

참가 물질

7

반응물 4

HCID 103713-PyridinecarboxaldehydeHCID 2724682Lithium diisopropylamideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 21973728Carbon dioxide methanol

생성물 1

HCID 73177292Ethyl 5-(pyridin-3-yl)-2,4-pentadienoate수율 89,098.398%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of LDA (16.5 ml of 2M solution, 3.5 g, 0.03 mol) in THF (100 ml) was cooled to −70° C. or below (dry ice-methanol bath) under a nitrogen flow and treated dropwise with ethyl 4-diethylphosphonocrotonate (8.6 g, 0.037 mmol) while stirring. The mixture was further stirred for 15 minutes, treated dropwise with nicotinaldehyde (3.2 g, 0.030 mol), and then stirred at 0° C. for 1.5 hours. Next, the mixture was treated with acetic acid and evaporated. To the residue was added saturated aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The extract was treated according to conventional techniques. Evaporation of solvent yielded ethyl 5-(pyridin-3-yl)penta-2,4-dienoate as an oil (6.7 g).

후처리

  1. stirringThe mixture was further stirred for 15 minutes
  2. stirringstirred at 0° C. for 1.5 hours
  3. customevaporated
  4. additionTo the residue was added saturated aqueous sodium hydrogen carbonate
  5. extractionthe mixture was extracted with ethyl acetate
  6. additionThe extract was treated
  7. customEvaporation of solvent

출처 및 근거

ORD 기록
ord-b1e8fe4b02d94af8afeefda62785ac90
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642250B2

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