碘化钠 → 4-Phenyl-1-trimethylsilyloxy-1-cyclohexene

HRID 12058

反应方程式

HRID 12058 反应方程式
[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

参与物

8

反应物 4

HCID 5238碘化钠HCID 6397三甲基氯硅烷HCID 8471三乙胺HCID 786054-苯基环己酮

产物 1

HCID 110860724-Phenyl-1-trimethylsilyloxy-1-cyclohexene收率 73%

试剂、催化剂与溶剂 3

HCID 6342乙腈溶剂HCID 8003正戊烷溶剂HCID 8058正己烷溶剂

实验过程

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]+.

后处理

  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

来源与证据

ORD记录
ord-03928dba07064fd18db97805e1109e87
来源数据集
uspto-grants-2010_06
专利号
US07727979B2

关联笔记

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