Hexane → N-[2-Ethyl-6-(3-oxo-6-phenyl-1-hexenyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 1734875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734875
[H-].[Na+].CCCCCC.C(OP([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([CH2:23][CH2:24][CH2:25][C:26](=[O:28])[CH3:27])[CH:22]=1)(OCC)=O)C.[CH2:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=O)[C:32]=1[NH:39][C:40](=[O:56])[CH2:41][CH:42]1[C:55]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[O:49][C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH3:30]>CN(C)C=O>[CH2:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[CH:27][C:26](=[O:28])[CH2:25][CH2:24][CH2:23][C:21]2[CH:22]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:32]=1[NH:39][C:40](=[O:56])[CH2:41][CH:42]1[C:55]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[O:49][C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH3:30]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 199659985-Diethoxyphosphoryl-1-(4-oxopentyl)benzeneHCID 19966259N-(2-ethyl-6-formylphenyl)-2-(9H-xanthen-9-yl)acetamide

Produkt 1

HCID 54326645N-[2-Ethyl-6-(3-oxo-6-phenyl-1-hexenyl)phenyl]-2-(9H-xanthen-9-yl)acetamideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

49 mg (1.13 mmol) of sodium hydride (as a 55% w/w suspension in mineral oil) were washed twice, each time with hexane, and were suspended in 6 ml of dimethylformamide. 2 ml of a dimethylformamide solution containing 289 mg (0.97 mmol) of 5-diethoxyphosphoryl-1-(4-oxopentyl)benzene were added to the suspension, whilst ice-cooling. The reaction mixture was then immediately allowed to return to room temperature, after which it was stirred for 30 minutes. 300 mg (0.808 mmol) of N-(2-ethyl-6-formylphenyl)-2-(9H-xanthen-9-yl)acetamide were then added to the reaction mixture, once again whilst ice-cooling. The mixture was then stirred for 1 hour at the ice-cooling temperature and then for 3 hours at room temperature. At the end of this time, the reaction solution was poured into ice-water and extracted with diethyl ether. The organic extract was washed with water. The solvent was removed by distillation under reduced pressure, and the resulting residue was recrystallized from a mixture of methylene chloride and diethyl ether, to give 220 mg (yield 53%) of the title compound as crystals, melting at 168°-170° C.

Aufarbeitung

  1. additionwere added to the suspension, whilst ice-
  2. temperaturecooling
  3. customto return to room temperature
  4. temperaturecooling
  5. temperaturecooling temperature
  6. waitfor 3 hours at room temperature
  7. extractionextracted with diethyl ether
  8. extractionThe organic extract
  9. washwas washed with water
  10. customThe solvent was removed by distillation under reduced pressure
  11. customthe resulting residue was recrystallized from a mixture of methylene chloride and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6a1f8d48638e46b2b4056f044f3aa35a
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534529

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