Hydrochloric Acid → HCID 14579488, compound

HRID 1607763Notes

Reaction equation

HRID 1607763 reaction equation
[F:1][CH2:2][C:3]([N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])([CH2:6][CH2:7][CH2:8][CH2:9][O:10]CC1C=CC=CC=1)[C:4]#[N:5].C[Si](I)(C)C.C(N(CC)CC)C.Cl>ClCCl.C(Cl)(Cl)Cl>[F:1][CH2:2][C:3]([N:18]1[C:19](=[O:28])[C:20]2=[CH:27][CH:26]=[CH:25][CH:24]=[C:21]2[C:22]1=[O:23])([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[C:4]#[N:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 14579487HCID 14579487, compound

Product 1

HCID 14579488HCID 14579488, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-fluoromethyl-2-phthalimido-6-benzyloxyhexanenitrile (15.5 g, 40.8 mmol) and trimethylsilyliodide (13 ml, 2.2 equivalents) in dry dichloromethane (100 ml) is stirred at room temperature under nitrogen overnight. After removing the solvent under vacuum, the residue is dissolved in dry chloroform, triethylamine (17 ml, 3 equivalents) is added, and the mixture is refluxed for 30 minutes. Upon cooling, the solution is stirred with 2N HCl (250 ml) for 15 minutes, the phases are separated, and the organic layer is washed with sodium bicarbonate and with water. After evaporation, the residue is dissolved in THF and water (20 ml). Drops of 6N HCl are added, and the resulting mixture is stirred for several minutes. The solvent is removed by evaporation, and the residue obtained in dissolved in chloroform, washed with water, and dried. Removal of solvent gives the crude title compound as an oil (12 g). Chromatography on silica (300 g, eluant: ethylacetate) gives 2-fluoromethyl-2-phthalimido-6-hydroxyhexanenitrile (9.0 g).

Workup

  1. customAfter removing the solvent under vacuum
  2. dissolutionthe residue is dissolved in dry chloroform
  3. temperaturethe mixture is refluxed for 30 minutes
  4. temperatureUpon cooling
  5. customthe phases are separated
  6. washthe organic layer is washed with sodium bicarbonate and with water
  7. customAfter evaporation
  8. dissolutionthe residue is dissolved in THF
  9. additionDrops of 6N HCl are added
  10. customThe solvent is removed by evaporation
  11. customthe residue obtained
  12. washwashed with water
  13. customdried
  14. customRemoval of solvent
  15. customgives the crude title compound as an oil (12 g)

Sources & evidence

ORD record
ord-227e78fb50e34b36bea3861b788a8fc5
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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