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

HRID 12058

Reaction equation

HRID 12058 reaction equation
[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

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 786054-Phenylcyclohexanone

Product 1

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

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8003PentaneSolventHCID 8058HexaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-03928dba07064fd18db97805e1109e87
Source dataset
uspto-grants-2010_06
Patent number
US07727979B2

Linked notes

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