HCID 20461683, compound → HCID 20461671, compound

HRID 543504Notes

Reaction equation

HRID 543504 reaction equation
[F:1][CH:2]([F:20])[CH:3]([N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])[CH2:4][C:5](=[CH2:8])[CH2:6]Br.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K]>CN(C)C=O>[F:1][CH:2]([F:20])[CH:3]([N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])[CH2:4][C:5](=[CH2:8])[CH2:6][N:25]1[C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]2[C:21]1=[O:31]

Participants

4

Reactant 2

HCID 20461683HCID 20461683, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 20461671HCID 20461671, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,1-difluoro-2-phthalimido-4-methylene-5-bromo-pentane (impure, evaluated 67 mmoles) prepared as in Step C above, and potassium phthalimide (13.9 g, 75 mmoles) is heated at 75° C. in dry N,N-dimethylformamide (DMF) (100 mL) for 3 hours. After removal of the DMF under vacuum, the residue is dissolved in chloroform and extracted with 1 N potassium hydroxide and three times with water. Work-up as described in Example 1(D) affords a colored oil (30 g, containing solvents) which is chromatographed on silica gel (petroleum ether/ether acetate: 70/30). The oil obtained (11.3 g) is crystallized from chloroform/ether/petroleum ether to give 1,1-difluoro-2,5-diphthalimido-4-methylene-pentane slightly contaminated (about 15%) by 1,1-difluoro-2,5-diphthalimido-4-methyl-3-pentene (7.9 g of mixture, yield based on 1,1-difluoro-2-phthalimido-4-methyl-4-pentene: 29%).

Workup

  1. customAfter removal of the DMF under vacuum
  2. dissolutionthe residue is dissolved in chloroform
  3. extractionextracted with 1 N potassium hydroxide and three times with water
  4. customaffords
  5. additiona colored oil (30 g, containing solvents) which
  6. customis chromatographed on silica gel (petroleum ether/ether acetate: 70/30)
  7. customThe oil obtained (11.3 g)
  8. customis crystallized from chloroform/ether/petroleum ether

Sources & evidence

ORD record
ord-5fc07249d9d24e0caa496677e0f82b59
Source dataset
uspto-grants-1984_05
Patent number
US04446151

Reaction notes

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