4-Pyridinylacetone → 6-Phenyl-3-(4-pyridinyl)hexa-3,5-dien-2-one

HRID 23543

反応式

HRID 23543 の反応式
[CH:1](=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](=[O:20])[CH3:19])=[CH:13][CH:12]=1>N1CCCCC1.C(O)(=O)C.C1(C)C=CC=CC=1>[C:4]1([CH:3]=[CH:2][CH:1]=[C:17]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)[C:18](=[O:20])[CH3:19])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 2

HCID 805524-PyridinylacetoneHCID 637511Cinnamaldehyde

生成物 1

HCID 538989266-Phenyl-3-(4-pyridinyl)hexa-3,5-dien-2-one収率 17%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 8082Piperidine触媒HCID 1140Toluene溶媒

実験手順

Trans-cinnamaldehyde (1.84 ml, 14.8 mmol), five drops of piperidine and five drops of acetic acid were added to a solution of 4-pyridyl acetone (2.0 g, 14.8 mmol) in toluene (25 ml). The mixture was heated to reflux for 48 hours with a Dean-Stark trap to remove water. The mixture was concentrated to give a black oil. The oil was purified by silica gel chromatography (eluted with 1:1 hexane/ethyl acetate). The desired fractions were collected, combined and concentrated to give 6-phenyl-3-(4-pyridinyl)hexa-3,5-dien-2-one (628 mg). The ketone was further purified by an additional column chromatography on silica gel (eluting with hexane-ethyl acetate-methylene chloride-methanol (1:1:2:0.12)) (380 mg, 27.3%): Anal. Calc'd for C17H15NO 0.4 H2O: C, 79.91; H, 5.84; N, 5.48. Found: C, 79.72; H, 5.91; N, 5.25. MS (M+H+): 250.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 hours with a Dean-Stark trap
  3. customto remove water
  4. concentrationThe mixture was concentrated
  5. customto give a black oil
  6. customThe oil was purified by silica gel chromatography (eluted with 1:1 hexane/ethyl acetate)
  7. customThe desired fractions were collected
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-76f21bb7c71f40d295b3b5201fb179c3
出典データセット
uspto-grants-2005_02
特許番号
US06852740B2

関連ノート

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