Methanol → 5-{N-[4-(4-methylstyryl)phenyl]-N-phenylamino}acenaphthene

HRID 1950

Reaktionsgleichung

Reaktionsgleichung von HRID 1950
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[C:26]3[C:27]4[C:19]([CH2:20][CH2:21][C:22]=4[CH:23]=[CH:24][CH:25]=3)=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)=O.[CH3:28][C:29]([CH3:32])([O-])[CH3:30].[K+].CO.O>CN(C)C=O>[CH3:28][C:29]1[CH:32]=[CH:4][C:3]([CH:8]=[CH:1][C:3]2[CH:8]=[CH:7][C:6]([N:9]([C:16]3[C:26]4[C:27]5[C:19]([CH2:20][CH2:21][C:22]=5[CH:23]=[CH:24][CH:25]=4)=[CH:18][CH:17]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:5][CH:4]=2)=[CH:1][CH:30]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 196889175-[N-(4-formylphenyl)-N-phenylamino]acenaphtheneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 676436125-{N-[4-(4-methylstyryl)phenyl]-N-phenylamino}acenaphtheneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

20.96 g (0.06 mol) of 5-[N-(4-formylphenyl)-N-phenylamino]acenaphthene prepared in Preparation Example 1 and 17.44 g (0.072 mol) of diethyl 4-methylbenzyl phosphonate were dissolved in 300 ml of N,N-dimethylformamide, and 10.1 g (0.09 mol) of potassium-tert-butoxide was added thereto at room temperature for 20 minutes. After the addition, the resultant mixture was further stirred for 2 hours. The reaction was determined to be finished when disappearance of the formyl compound was identified. The reaction product was poured into 1500 ml of methanol at a temperature of 5° C. or lower, and 150 ml of water was further dropwise added thereto to precipitate a crystal, which was then filtrated, washed with methanol and dried to obtain 22.18 g (yield: 84.5%) of a crude crystal. 21.0 g of the crude crystal thus obtained was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4) to obtain 17.85 g of (purification yield: 85.0%, melting point: 148.0°-149.0° C.) of 5-{N-[4-(4-methylstyryl)phenyl]-N-phenylamino}acenaphthene (Compound No. 4).

Aufarbeitung

  1. additionAfter the addition
  2. customto precipitate a crystal, which
  3. filtrationwas then filtrated
  4. washwashed with methanol
  5. customdried
  6. customto obtain 22.18 g (yield: 84.5%) of a crude crystal
  7. custom21.0 g of the crude crystal thus obtained
  8. customwas purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4)

Quellen und Nachweise

ORD-Eintrag
ord-b58f8f3df4214a82901f48cbd358ba6b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728500

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