Dimethylformamide → N-(4-benzyloxy-2,2-difluorobutyl)phthalimide

HRID 232170Notes

Reaction equation

HRID 232170 reaction equation
CS(O[CH2:6][C:7]([F:19])([F:18])[CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)=O.CN(C=O)C.[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.[K]>O>[CH2:11]([O:10][CH2:9][CH2:8][C:7]([F:19])([F:18])[CH2:6][N:29]1[C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]2[C:25]1=[O:35])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 149977751-Methanesulfonyloxy-2,2-difluoro-4-benzyloxybutaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 19860700N-(4-benzyloxy-2,2-difluorobutyl)phthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

The compound 1-methanesulfonyloxy-2,2-difluoro-4-benzyloxybutane (21.8 g, 74.1 mM), dry DMF (100 mL), and potassium phthalimide (15.26 g, 10% excess) are stirred and heated under nitrogen, at 120° C. for 5 days. Following the addition of water (500 mL), the mixture is extracted with ether. The organic phase is washed with 1N CCl followed by water (twice), dried (Na2SO4) and concentrated to a volume of about 100 mL. Upon addition of petroleum ether, crystallization occurs. After chilling for 3 hours at 5° C., beige crystals of the compound N-(4-benzyloxy-2,2-difluorobutyl)phthalimide are obtained, filtered and washed with petroleum ether: 18 g (70%).

Workup

  1. extractionthe mixture is extracted with ether
  2. washThe organic phase is washed with 1N CCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to a volume of about 100 mL
  5. additionUpon addition of petroleum ether, crystallization
  6. temperatureAfter chilling for 3 hours at 5° C.

Sources & evidence

ORD record
ord-c051ca12991a463d80a3283f8c1fb1b3
Source dataset
uspto-grants-1989_07
Patent number
US04851448

Reaction notes

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