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

HRID 2085890노트

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HRID 2085890 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 538517063,5-Bis(3',5'-di-t-butylstyryl)styrene수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 (36 H, s, tBu), 5.34 (1 H, d, J 11, 8-H), 5.88 (1 H, d, J 18, 8-H), 6.79 (1 H, dd, J 11 and 18, 7-H), 7.15 (2 H, d, J 16, 7′-H), 7.25 (2H, d, J 16, 8′-H), 7.38 (2 H, t, J 1.75, 1′-H), 7.42 (4 H, d, J 1.75, 3′,5′-H), 7.49 (2 H, d, J 1.3, 3,5-H), 7.63 (1H, m, 1-H).

후처리

  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

출처 및 근거

ORD 기록
ord-d08dffb2bf434503a14d6ae83d659690
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720093B2

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