Dimethylformamide → 9,10-Bis[3',5'-bis(3'',5''-di-t-butylstyryl)styryl]anthracene

HRID 411935Notes

Reaction equation

HRID 411935 reaction equation
CN(C)C=O.[CH3:6][C:7]([CH3:10])([O-])[CH3:8].[K+].[C:12]([C:16]1[CH:17]=[C:18]([CH:45]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:47]=1)[CH:19]=[CH:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([CH:29]=[CH:30][C:31]2[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:34]=[C:33]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:32]=2)[CH:28]=1)[CH:24]=O)([CH3:15])([CH3:14])[CH3:13]>CO>[C:12]([C:16]1[CH:17]=[C:18]([CH:45]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:47]=1)[CH:19]=[CH:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([CH:29]=[CH:30][C:31]2[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:34]=[C:33]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:32]=2)[CH:28]=1)[CH:24]=[CH:6][C:7]1[C:10]2[C:8]([C:7]([CH:6]=[CH:24][C:23]3[CH:26]=[C:27]([CH:29]=[CH:30][C:31]4[CH:32]=[C:33]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:34]=[C:35]([C:37]([CH3:38])([CH3:39])[CH3:40])[CH:36]=4)[CH:28]=[C:21]([CH:20]=[CH:19][C:18]4[CH:45]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:47]=[C:16]([C:12]([CH3:13])([CH3:14])[CH3:15])[CH:17]=4)[CH:22]=3)=[C:10]3[C:8]=1[CH:20]=[CH:19][CH:18]=[CH:17]3)=[CH:47][CH:16]=[CH:12][CH:13]=2)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 23665647Potassium tert-butoxideHCID 540286873,5-Bis[2-(3,5-di-tert-butylphenyl)ethenyl]benzaldehyde

Product 1

HCID 542881889,10-Bis[3',5'-bis(3'',5''-di-t-butylstyryl)styryl]anthraceneYield 26.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dry N,N-dimethylformamide (10 ml) was added to a rapidly stirred mixture of 9,10-bis(dimethylmethylphosphonate)anthracene (395 mg, 0.935 mmoles), potassium t-butoxide (220 mg, 1.963 mmoles) and 3,5-bis(3′,5′-di-t-butylstyryl)benzaldehyde (1.000 g, 1.87 mmoles) under nitrogen and stirred at room temperature for 90 minutes. Distilled methanol (60 ml) was then added and the precipitate filtered and dried under suction. The crude product (925 mg) was recrystallized from dichloromethane-methanol and then chromatographed on flash silica using dichloromethane-pet. ether (40-60) (1:3) as the eluent. The solvent was removed to give 9,10-bis[3′,5′-bis(3″,5″-di-t-butylstyryl)styryl]anthracene (206 mg, 18%). lamdamax(film)/nm 308, 420.

Workup

  1. filtrationthe precipitate filtered
  2. customdried under suction
  3. customThe crude product (925 mg) was recrystallized from dichloromethane-methanol
  4. customchromatographed on flash silica
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-c265693ed630465b95f777838c7a03a5
Source dataset
uspto-grants-2003_05
Patent number
US06558818B1

Reaction notes

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