Sodium Iodide → 4-Cyano-5-methyl-4-phenylhexyl Iodide

HRID 1582762Notes

Reaction equation

HRID 1582762 reaction equation
[C:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].S(Cl)(C)(=O)=O.[I-:22].[Na+]>C(#N)C.C(N(CC)CC)C>[C:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6][I:22])#[N:2]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 31297Methanesulfonyl chlorideHCID 101306314-Cyano-5-methyl-4-phenylhexanol

Product 1

HCID 223936654-Cyano-5-methyl-4-phenylhexyl Iodide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

5.00 g 23.0 mmol of 4-Cyano-5-methyl-4-phenylhexanol disclosed in Example 2 or 3 of JP 11-70613-A was added to and dissolved in acetonitrile 150 ml and triethylamine 3.53 ml. Mesyl chloride, 1.96 ml 25.3 mmol, was added thereto. After 25 minutes, sodium iodide 20.7 g was added thereto. The reaction mixture was partitioned by adding brine and ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate and then with brine, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 5. 89 g 18.0 mmol, 78.2%, was obtained as a pale yellow oil.

Workup

  1. additionwas added to and
  2. customThe reaction mixture was partitioned
  3. additionby adding brine and ethyl acetate
  4. washThe organic layer was washed with aqueous sodium thiosulfate
  5. dry with materialwith brine, dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 5
  8. custom89 g 18.0 mmol, 78.2%, was obtained as a pale yellow oil

Sources & evidence

ORD record
ord-ee1d669f9bff4bacb42ff89245eaa878
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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