Trimethylsilyl iodide → 2-Fluoromethyl-2-phthalimido-5-iodopentanenitrile

HRID 977298Notes

Reaction equation

HRID 977298 reaction equation
[F:1][CH2:2][C:3]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([CH2:6][CH2:7][CH2:8]OC)[C:4]#[N:5].C[Si]([I:26])(C)C>C(Cl)(Cl)Cl>[F:1][CH2:2][C:3]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([CH2:6][CH2:7][CH2:8][I:26])[C:4]#[N:5]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 199663292-Fluoromethyl-2-phthalimido-5-methoxypentanenitrile

Product 1

HCID 147716572-Fluoromethyl-2-phthalimido-5-iodopentanenitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Fluoromethyl-2-phthalimido-5-methoxy-valeronitrile (1.20 g, 4.14 mmol), trimethylsilyl iodide (3.2 g, 16 mmol) and chloroform (15 mL) are heated to 60° C. under nitrogen for 48 hours. After removal of the solvent, the residue is dissolved in chloroform, washed with water, sodium thiosulfate solution and water again, dried and evaporated to give the crude product as an oil (1.2 g). This is purified by chromatography on silica (ethyl acetate/petroleum ether 1:3) to give pure 2-fluoromethyl-2-phthalimido-5-iodo-valeronitrile. NMR (CDCl3) δ: 2.0 (4H, m), 3.10 (2H, t), 4.90 (2H, ABX, JAB =9 Hz, JAX =JBX =JH-F =46 Hz), 7.70 (4H, s).

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue is dissolved in chloroform
  3. washwashed with water, sodium thiosulfate solution and water again
  4. customdried
  5. customevaporated
  6. customto give the crude product as an oil (1.2 g)
  7. customThis is purified by chromatography on silica (ethyl acetate/petroleum ether 1:3)

Sources & evidence

ORD record
ord-956c164c93e84919bd163f302e661ed6
Source dataset
uspto-grants-1997_03
Patent number
US05614557

Reaction notes

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