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

HRID 977833Notes

Reaction equation

HRID 977833 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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 m9 (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.

Workup

  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

Sources & evidence

ORD record
ord-8210f4560f3b4e1eb4a5870e15bb304a
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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