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 724353Notes

Reaction equation

HRID 724353 reaction equation
[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]

Participants

8

Reactant 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, compoundHCID 178418339Butyllithium

Product 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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b8ec458f7a2a4c9aab0adfd0bd47c954
Source dataset
uspto-grants-2006_11
Patent number
US07141637B2

Reaction notes

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