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

HRID 12058

反応式

HRID 12058 の反応式
[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

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 786054-Phenylcyclohexanone

生成物 1

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

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8003Pentane溶媒HCID 8058Hexane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-03928dba07064fd18db97805e1109e87
出典データセット
uspto-grants-2010_06
特許番号
US07727979B2

関連ノート

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