Sodium Iodide → 4-Phenyl-1-trimethylsilyloxy-1-cyclohexene

HRID 12058

반응식

HRID 12058 반응식
[I-].[Na+].[C:3]1([CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:23][Si:24]([CH3:27])([CH3:26])Cl>C(#N)C.CCCCCC.CCCCC>[CH3:23][Si:24]([CH3:27])([CH3:26])[O:15][C:12]1[CH2:13][CH2:14][CH:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][CH:11]=1

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 786054-Phenylcyclohexanone

생성물 1

HCID 110860724-Phenyl-1-trimethylsilyloxy-1-cyclohexene수율 73%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8003Pentane용매HCID 8058Hexane용매

실험 절차

sodium iodide (12.4 mmol) dissolved in acetonitrile (12.4 ml), is added dropwise at room temperature to a solution of 4-phenylcyclohexanone (10 mmol) in hexane (10 ml), followed by triethylamine (12.4 mmol) and trimethylchlorosilane (12.4 mmol). After stirring for two hours cold pentane and ice water are added. The aqueous phase is extracted with hexane. The combined organic phases are washed with ice water, dried over sodium sulphate and the solvent is removed in a vacuum. Trimethyl-(4-phenyl-cyclohex-1-enyloxy)-silane (1.8 g) is obtained in pure form in a yield of 73% (Tetrahedron 1987, 43, 9, 2075-2088): tR 2.29 min (LC-2); ESI-MS (+): m/z 247.27 [M+H]+.

후처리

  1. additionare added
  2. extractionThe aqueous phase is extracted with hexane
  3. washThe combined organic phases are washed with ice water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is removed in a vacuum

출처 및 근거

ORD 기록
ord-03928dba07064fd18db97805e1109e87
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727979B2

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