Sodium Iodide → 1-Iodo-4-methyl-4-nitro-pentane

HRID 33385Notes

Reaction equation

HRID 33385 reaction equation
C[Si](C)(C)Cl.[CH3:6][C:7]([N+:13]([O-:15])=[O:14])([CH3:12])[CH2:8][CH2:9][CH2:10]O.[I-:16].[Na+]>C(#N)C>[I:16][CH2:10][CH2:9][CH2:8][C:7]([CH3:12])([N+:13]([O-:15])=[O:14])[CH3:6]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 228070Pentanol, 4-methyl-4-nitro-

Product 1

HCID 99430631-Iodo-4-methyl-4-nitro-pentane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

70 mL (0.544 mol) trimethylchlorosilane are added dropwise at ambient temperature to 40 g (0.272 mol) 4-methyl-4-nitro-pentan-1-ol and 81.5 g (0.544 mol) sodium iodide in 350 mL acetonitrile. The reaction mixture is filtered, evaporated down and combined with diethyl ether. The organic phase is washed with sodium bisulphite solution and water, dried and freed from the solvent. Yellow oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated down
  3. washThe organic phase is washed with sodium bisulphite solution and water
  4. customdried

Sources & evidence

ORD record
ord-2796280100474c2e90eec5d439da496f
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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