Cyclopentene, 1-[(trimethylsilyl)oxy]- → HCID 54065381, Verbindung

HRID 1742185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742185
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:53](=[O:56])[CH:54]=[CH2:55])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Si](C)(C)[O:59][C:60]1[CH2:64][CH2:63][CH2:62][CH:61]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=[N:30][N:29]=3)=[CH:20][CH:21]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:53](=[O:56])[CH2:54][CH2:55][CH:61]3[CH2:62][CH2:63][CH2:64][C:60]3=[O:59])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 2

HCID 88326Cyclopentene, 1-[(trimethylsilyl)oxy]-HCID 54567513HCID 54567513, Verbindung

Produkt 1

HCID 54065381HCID 54065381, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 0.201 g of the product of Example 3 in 4.5 ml of methylene chloride, cooled to -78° C., is added dropwise 0.549 ml of 1.0M TiCl4 in methylene chloride. The reaction mixture is stirred at -78° C. for 30 minutes and 0.098 ml of 1-(trimethylsilyloxy)-cyclopentene added dropwise. The reaction mixture is stirred at -78° C., for 0.5 hours and quenched with saturated potassium carbonate, diluted with chloroform, filtered through magnesium sulfate and concentrated in vacuo to give a residue which is purified by chromatography on silica gel by elution with 1:3 ethyl acetatehexane to give 0.079 g of the desired product as a white solid.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at -78° C., for 0.5 hours
  2. customquenched with saturated potassium carbonate
  3. additiondiluted with chloroform
  4. filtrationfiltered through magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customis purified by chromatography on silica gel by elution with 1:3 ethyl acetatehexane

Quellen und Nachweise

ORD-Eintrag
ord-e9d72c9555e9474f85f3c02386e59a39
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05338736

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