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

HRID 1995566Notes

Reaction equation

HRID 1995566 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-benzyloxy-valeronitrile (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, 1 N HCl (2×), water again, drying, and evaporation gives the title compound 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, 1 N HCl (2×), water again
  7. customdrying
  8. customevaporation

Sources & evidence

ORD record
ord-2a5db6dcaba84139a3b1efcefe979c78
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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