Ammonium Chloride → Dimethyl-(4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacenyl)(2-i-propyl-4-phenyl-1-indenyl)-silane

HRID 271796ノート

反応式

HRID 271796 の反応式
[C:1]1([C:7]2[C:18]3[CH2:17][C:16]([CH3:19])=[CH:15][C:14]=3[CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Cl[Si:26]([CH:29]1[C:37]2[C:32](=[C:33]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[CH:44]([CH3:46])[CH3:45])([CH3:28])[CH3:27].[Cl-].[NH4+]>C(OCC)C.CCCCCC.[Cu](C#N)C#N>[CH3:27][Si:26]([CH3:28])([CH:11]1[C:12]2[C:8](=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:18]3[CH2:17][C:16]([CH3:19])=[CH:15][C:14]=3[CH:13]=2)[CH2:9][CH2:10]1)[CH:29]1[C:37]2[C:32](=[C:33]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[CH:44]([CH3:45])[CH3:46]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 534453466-Methyl-4-phenyl-1,2,3,5-tetrahydro-s-indaceneHCID 68744992Chloro-(2-i-propyl-4-phenyl-indenyl)-dimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 68745586Dimethyl-(4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacenyl)(2-i-propyl-4-phenyl-1-indenyl)-silane収率 104.3%

試薬・触媒・溶媒 3

HCID 178418260HCID 178418260、化合物触媒HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

To 12.3 g (50 mmol) of 4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacene (2b) and 150 mg (1.5 mmol) of copper cyanide (I) in 450 ml of diethylether was added dropwise at −70° C. 23 ml (57 mmol) of 2.5 M of n-butyllithium in n-hexane. The solution was slowly warmed to room temperature and stirred for 3 hrs at room temperature. Then to the solution was added at −70° C. 16.4 g (50 mmol) of chloro-(2-i-propyl-4-phenyl-indenyl)-dimethylsilane and the solution was warmed to room temperature and stirred for 5 hrs. The resulting back slurry solution was poured into an aqueous ammonium chloride solution and the organic layer was washed with brine, dried over sodium sulfate and the solvents were evaporated to give 28 g of crude product. This was purified by column chromatography (800 g of silica gel, 101 Heptane:CH2Cl2=5:1). Yield: 9.5 g (35%)

後処理

  1. additionThen to the solution was added at −70° C
  2. stirringstirred for 5 hrs
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were evaporated

出典と根拠

ORDレコード
ord-0655d291149141199cfe92ce5ecfcf50
出典データセット
uspto-grants-2008_11
特許番号
US07452949B2

反応ノート

読み込み中…