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

HRID 1007759

반응식

HRID 1007759 반응식
[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

참가 물질

6

반응물 4

HCID 241BenzeneHCID 243Benzoic AcidHCID 710273,3-DiphenylacroleinHCID 68574662HCID 68574662, 화합물

생성물 1

HCID 53936700Ethyl 5,5-diphenylpenta-2,4-dienoate수율 82.4%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5e062507c5c34e06be7b61cd6e4e2387
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06797711B2

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