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

HRID 271796노트

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HRID 271796 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418260HCID 178418260, 화합물촉매HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-0655d291149141199cfe92ce5ecfcf50
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452949B2

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