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

HRID 411931ノート

反応式

HRID 411931 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 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Dry tetrahydrofuran (300 ml) was added to a mixture of methyltriphenylphosphonium iodide (17.00 g, 42.0 mmoles) and potassium t-butoxide (4.72 g, 42.0 mmoles) and stirred at room temperature for 10 minutes. 3,5-bis(3′,5′-di-t-butylstyryl)benzaldehyde (17.00 g, 42.0 mmoles) was then added and the reaction mixture was stirred at room temperature for 75 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 solvent was evaporated to give 3,5-bis(3′,5′-di-t-butylstyryl)styrene (14.83 g, 99%), mp 150° C. (Found: C, 90.03; H, 9.98. C40H52 requires C, 90.16; H, 9.84%); λmax(CHCl3)/nm 318 (ε/dm3 mol-1 cm-1 68500); δH(500 MHz; CDCl3) 1.39 (36H, s, tBu), 5.34 (1H, d, J 11, 8-H), 5.88 (1H, d, J 18, 8-H), 6.79 (1H, dd, J 11 and 18, 7-H), 7.15 (2H, d, J 16, 7′-H), 7.25 (2H, d, J 16, 8′-H), 7.38 (2H, t, J 1.75, 1′-H), 7.42 (4H, d, J 1.75, 3′, 5′-H), 7.49 (2H, d, J 1.3, 3,5-H), 7.63 (1H, m, 1-H).

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 75 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 solvent was evaporated

出典と根拠

ORDレコード
ord-a4483e7901e04a70aeec0449238f57e2
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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