Hexane → [3-(4-tert-butyl-phenyl)-2,5-dimethyl-6H-cyclopenta[b]thiophen-6-yl]-[4-(4-tert-butyl-phenyl)-2-isopropyl-1H-inden-1-yl]-dimethyl-silane

HRID 724353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724353
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[CH2:19][C:18]([CH3:20])=[CH:17][C:13]=3[S:14][C:15]=2[CH3:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.[Cu](C#N)C#N.Cl[Si:38]([CH:41]1[C:49]2[C:44](=[C:45]([C:50]3[CH:55]=[CH:54][C:53]([C:56]([CH3:59])([CH3:58])[CH3:57])=[CH:52][CH:51]=3)[CH:46]=[CH:47][CH:48]=2)[CH:43]=[C:42]1[CH:60]([CH3:62])[CH3:61])([CH3:40])[CH3:39].[Cl-].[NH4+]>C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]3[CH:19]=[C:18]([CH3:20])[CH:17]([Si:38]([CH:41]4[C:49]5[C:44](=[C:45]([C:50]6[CH:51]=[CH:52][C:53]([C:56]([CH3:58])([CH3:57])[CH3:59])=[CH:54][CH:55]=6)[CH:46]=[CH:47][CH:48]=5)[CH:43]=[C:42]4[CH:60]([CH3:62])[CH3:61])([CH3:39])[CH3:40])[C:13]=3[S:14][C:15]=2[CH3:16])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 6

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 218803283-(4-tert-Butyl-phenyl)-2,5-dimethyl-4H-cyclopenta[b]thiopheneHCID 21880365chloro-(4-(4-tert-butylphenyl)-2-isopropyl-1H-inden-1-yl)-dimethylsilaneHCID 178418260HCID 178418260, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 21880339[3-(4-tert-butyl-phenyl)-2,5-dimethyl-6H-cyclopenta[b]thiophen-6-yl]-[4-(4-tert-butyl-phenyl)-2-isopropyl-1H-inden-1-yl]-dimethyl-silane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution containing 5.64 g (20 mmol) 3-(4-tert-Butyl-phenyl)-2,5-dimethyl-4H-cyclopenta[b]thiophene dissolved in 50 ml of diethyl ether was added a 2.5 M solution of n-butyllithium in hexane (20 mmol, 8 ml). A catalytic amount of copper cyanide was added (0.08 g), then the reaction mixture was stirred for 3 h. The temperature was reduced to −78° C., then a solution containing 7.66 g (20 mmol) chloro-(2-isopropyl-4-(4-tert-butyl-phenyl)-1H-inden-1-yl)-dimethyl-silane dissolved in 20 ml diethyl ether was added drop-wise. After addition was complete, the flask was allowed to warm to room temperature and stirring was continued for 5 h, then poured into a saturated solution of ammonium chloride. The organic fraction was collected with a 30% dichloromethane/70% hexane solution, washed with 2N HCl, saturated bicarbonate, water, then dried over magnesium sulfate. The reaction product was filtered, then solvents removed in vacuo. Yield: 11.92 g (92%) light orange powder.

Aufarbeitung

  1. customwas reduced to −78° C.
  2. additionwas added drop-wise
  3. additionAfter addition
  4. stirringstirring
  5. waitwas continued for 5 h
  6. customThe organic fraction was collected with a 30% dichloromethane/70% hexane solution
  7. washwashed with 2N HCl, saturated bicarbonate, water
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe reaction product was filtered
  10. customsolvents removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b8ec458f7a2a4c9aab0adfd0bd47c954
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141637B2

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