Benzene → HCID 86759055, compound

HRID 1356802Notes

Reaction equation

HRID 1356802 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CCCCCC.[CH3:12][C:13]([CH3:32])([CH3:31])[C:14]#[C:15]/[CH:16]=[CH:17]/[CH2:18][N:19]([CH2:21]C1C=C(C(=O)C)C=CC=1)[CH3:20].[CH:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH3:12][C:13]([CH3:31])([CH3:32])[C:14]#[C:15]/[CH:16]=[CH:17]\[CH2:18][N:19]([CH2:21][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:2]([CH3:1])=[CH:3][CH3:4])[CH:34]=1)[CH3:20]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8058HexaneHCID 12069881HCID 12069881, compoundHCID 178418339Butyllithium

Product 1

HCID 86759055HCID 86759055, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

Ethyl triphenylphosphonium bromide (0.98 g; 2.65 mmol) was added to benzene (15 ml). While the mixture was stirred under nitrogen atmosphere at room temperature, n-butyl lithium in n-hexane (1.56 M: 1.70 ml; 2.65 mmol) was added dropwise. The mixture was stirred for 5 minutes, and Compound 1 (0.50 g; 1.76 mmol) in benzene (5 ml) was added dropwise thereto, followed by heating under reflux for 3 hours. Subsequently, the mixture was left to cool to room temperature, and reaction was stopped by pouring the mixture into ice/water, followed by extraction with benzene (100 ml). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), to thereby yield 0.13 g of the target compound (yield: 25.0%).

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. temperatureby heating
  3. temperatureunder reflux for 3 hours
  4. waitSubsequently, the mixture was left
  5. temperatureto cool to room temperature
  6. customreaction
  7. extractionfollowed by extraction with benzene (100 ml)
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-4b53d333af7149caa2c8a2067b60cb96
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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