Methyltriphenylphosphonium iodide → 3,5-Bis(3',5'-di-t-butylstyryl)styrene

HRID 411932ノート

反応式

HRID 411932 の反応式
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:28]([C:32]1[CH:33]=[C:34]([CH:61]=[C:62]([C:64]([CH3:67])([CH3:66])[CH3:65])[CH:63]=1)[CH:35]=[CH:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([CH:45]=[CH:46][C:47]2[CH:52]=[C:51]([C:53]([CH3:56])([CH3:55])[CH3:54])[CH:50]=[C:49]([C:57]([CH3:60])([CH3:59])[CH3:58])[CH:48]=2)[CH:44]=1)[CH:40]=O)([CH3:31])([CH3:30])[CH3:29]>O1CCCC1>[C:28]([C:32]1[CH:33]=[C:34]([CH:61]=[C:62]([C:64]([CH3:67])([CH3:66])[CH3:65])[CH:63]=1)[CH:35]=[CH:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([CH:45]=[CH:46][C:47]2[CH:52]=[C:51]([C:53]([CH3:56])([CH3:55])[CH3:54])[CH:50]=[C:49]([C:57]([CH3:60])([CH3:59])[CH3:58])[CH:48]=2)[CH:44]=1)[CH:40]=[CH2:2])([CH3:31])([CH3:30])[CH3:29]

参加物

5

反応物 3

HCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 540286873,5-Bis[2-(3,5-di-tert-butylphenyl)ethenyl]benzaldehyde

生成物 1

HCID 538517063,5-Bis(3',5'-di-t-butylstyryl)styrene収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Dry tetrahydrofuran (375 mL) was added to a mixture of methyltriphenylphosphonium iodide (50.6 g, 125 mmoles) and potassium t-butoxide (14.0 g, 125 mmoles) and stirred at room temperature for 15 minutes. 3,5-bis(3′,5′-di-t-butylstyryl)benzaldehyde (44.6 g, 83.4 mmoles) was then added and the reaction mixture was stirred at room temperature for 90 minutes. The solvent was then evaporated and the remaining sludge was triturated with dichloromethane-pet.ether (40-60) (1:9) and filtered through silica, rinsing thoroughly with the same solvent mixture. The crude product was recrystallised from dichloromethane/methanol to give white crystals of 3,5-bis(3′,5′-di-t-butylstyryl)styrene (42.15 g, 95%) m.p. 143-145° C. with microanalysis i/r, u/v, NMR and mass spectrographic data substantially identical to that of the first example.

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 90 minutes
  2. customThe solvent was then evaporated
  3. customthe remaining sludge was triturated with dichloromethane-pet
  4. filtrationether (40-60) (1:9) and filtered through silica
  5. washrinsing thoroughly with the same solvent mixture
  6. customThe crude product was recrystallised from dichloromethane/methanol

出典と根拠

ORDレコード
ord-4860cb35bd794a1491f259d2134c0638
出典データセット
uspto-grants-2003_05
特許番号
US06558818B1

反応ノート

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