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 724353ノート

反応式

HRID 724353 の反応式
[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]

参加物

8

反応物 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、化合物HCID 178418339Butyllithium

生成物 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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b8ec458f7a2a4c9aab0adfd0bd47c954
出典データセット
uspto-grants-2006_11
特許番号
US07141637B2

反応ノート

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