Benzaldehyde → (E)-3-Phenyl-1-(pyridin-2-yl)prop-2-en-1-one

HRID 1815126노트

반응식

HRID 1815126 반응식
[OH-].[Na+].C(O)C.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(=[O:8])[CH3:7].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH:19]1[CH:20]=[CH:21][C:16](/[CH:15]=[CH:7]/[C:6]([C:9]2[N:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 702EthanolHCID 142862-AcetylpyridineHCID 14798Sodium Hydroxide

생성물 1

HCID 5354119(E)-3-Phenyl-1-(pyridin-2-yl)prop-2-en-1-one

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of NaOH (12.8 mmol, 1.28 equiv.) in water (4.55 g) and ethanol (2.32 g) are introduced into a round bottom flask with a magnetic stirrer. Into the alkaline solution is placed 2-acetyl pyridine 1a (10 mmol, 1 equiv.) and the flask is rapidly surrounded by ice and the stirrer is started. The temperature reaches 10° C.-15° C. and benzaldehyde 1b (10 mmol, 1 equiv.) is added at once. The ice bath is removed and the reaction is stirred for 15 hours. The reaction is filtered. The filtrate is concentrated under reduced pressure and the product is purified by flash column chromatography on SiO2 (33% ethyl acetate/hexanes) to give the 3-phenyl-1-pyridin-2-yl-propenone 1c as a pale yellow solid. See Kohler, E. P. & H. M. Chadwell, H. M., Org. Synth., Coll. Vol. 1, 2nd ed., p. 78.

후처리

  1. customreaches 10° C.-15° C.
  2. customThe ice bath is removed
  3. filtrationThe reaction is filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe product is purified by flash column chromatography on SiO2 (33% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-c403e5ab99ad4f84991ed747de072f39
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878729B2

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