Benzene → Ethyl 5,5-diphenylpenta-2,4-dienoate

HRID 1007759

反応式

HRID 1007759 の反応式
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([CH:22]=C1CCP(C2C=CC=CC=2)C1(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18].C(O)(=O)C1C=CC=CC=1.C1C=CC=CC=1>CCCCCC>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=[CH:22][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 241BenzeneHCID 243Benzoic AcidHCID 710273,3-DiphenylacroleinHCID 68574662HCID 68574662、化合物

生成物 1

HCID 53936700Ethyl 5,5-diphenylpenta-2,4-dienoate収率 82.4%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

β-Phenylcinnamaldehyde (3.36 g), (carbethoxymethylene)triphenylphospholane (5.68 g), and benzoic acid (0.2 g) were added to anhydrous benzene (80 mL), and the mixture was refluxed under stirring for 3.5 hours. Subsequently, the resultant mixture was cooled to room temperature and condensed under reduced pressure. n-Hexane was added to the residue, and the insoluble matter was collected through filtration and washed several times with n-hexane. The filtrate and the resulting wash liquid were combined and condensed under reduced pressure. The product was purified through silica gel column chromatography (silica gel 40 g, eluent; n-hexane:ethyl acetate=50:1), to thereby yield 3.70 g of the product of interest (yield 82.4%).

後処理

  1. temperaturethe mixture was refluxed
  2. customcondensed under reduced pressure
  3. filtrationthe insoluble matter was collected through filtration
  4. washwashed several times with n-hexane
  5. washThe filtrate and the resulting wash liquid
  6. customcondensed under reduced pressure
  7. customThe product was purified through silica gel column chromatography (silica gel 40 g, eluent; n-hexane:ethyl acetate=50:1)

出典と根拠

ORDレコード
ord-5e062507c5c34e06be7b61cd6e4e2387
出典データセット
uspto-grants-2004_09
特許番号
US06797711B2

関連ノート

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