Oxygen → HCID 515320, compound

HRID 461966Notes

Reaction equation

HRID 461966 reaction equation
[CH2:1]([N:3]([CH2:34][CH3:35])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][C:16]([C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=1)=[O:9])[CH3:2].[OH-:36].C([N+](C)(C)C)C1C=CC=CC=1.O=O>N1C=CC=CC=1>[CH2:34]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][C:16]([C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])=[CH:17][CH:18]=3)[C:13](=[O:36])[C:12]=2[CH:11]=1)=[O:9])[CH3:35]

Participants

5

Reactant 3

HCID 977OxygenHCID 66854Benzyltrimethylammonium hydroxideHCID 515309HCID 515309, compound

Product 1

HCID 515320HCID 515320, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 12.0g (0.025 mole) 2,7-bis[5-(diethylamino)valeryl]-fluorene, prepared in Example 16, 2.0 ml 40% benzyltrimethylammonium hydroxide in pyridine and 200 ml pyridine was stirred at room temperature while oxygen was bubbled through the solution at a rate of 500 ml/min. for a total of four hours. The reaction mixture was evaporated to dryness leaving a residue which was chromatographed on alumina using chloroform as the eluant. The solvent was removed from the fraction collected leaving a solid which was recrystallized once from chloroform-petroleum ether to yield the desired product. M.P. 108°-109.5° C, λmaxEtOH 280, E1cm1% 1530.

Workup

  1. customwas bubbled through the solution at a rate of 500 ml/min. for a total of four hours
  2. customThe reaction mixture was evaporated to dryness
  3. customleaving a residue which
  4. customwas chromatographed on alumina
  5. customThe solvent was removed from the fraction
  6. customcollected
  7. customleaving a solid which
  8. customwas recrystallized once from chloroform-petroleum ether

Sources & evidence

ORD record
ord-9ea60bfd231c41c0a1e82bda842aef16
Source dataset
uspto-grants-1977_12
Patent number
US04064347

Reaction notes

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