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

HRID 1252568Notes

Reaction equation

HRID 1252568 reaction equation
[F:1][CH2:2][C:3]([N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])([CH2:6][CH2:7][CH2:8][O:9]CC1C=CC=CC=1)[C:4]#[N:5].[Si](I)(C)(C)C>ClCCl>[F:1][CH2:2][C:3]([N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])([CH2:6][CH2:7][CH2:8][OH:9])[C:4]#[N:5]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 147716542-Fluoromethyl-2-phthalimido-5-benzyloxypentanenitrile

Product 1

HCID 147716552-Fluoromethyl-2-phthalimido-5-hydroxypentanenitrileYield 114.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-fluoromethyl-2-phthalimido-5-benzyloxypentanenitrile (49.4 g) in dry dichloromethane (400 ml) is added TMSI (45 ml, 2.2 equivalents), and the mixture is stirred at room temperature overnight. The solvent is removed under vacuum. The residue is evaporated two times more with dichloromethane and then dissolved in chloroform. After addition of triethylamine (60 ml), the mixture is refluxed for 3 hours. Washing with water, 1N HCl (2×), water again, drying, and evaporation gives 2-fluoromethyl-2-phthalimido-5-hydroxypentanenitrile as a brown oil (42.8 g).

Workup

  1. customThe solvent is removed under vacuum
  2. customThe residue is evaporated two times more with dichloromethane
  3. dissolutiondissolved in chloroform
  4. additionAfter addition of triethylamine (60 ml)
  5. temperaturethe mixture is refluxed for 3 hours
  6. washWashing with water, 1N HCl (2×), water again
  7. customdrying
  8. customevaporation

Sources & evidence

ORD record
ord-afa9da7b80f44590817d46dd85146131
Source dataset
uspto-grants-1988_05
Patent number
US04743691

Reaction notes

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