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

HRID 1607757Notes

Reaction equation

HRID 1607757 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-0c627c175eb344cf8422eb07be40d194
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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