2,2-Difluoro-3-Tetrahydropyranyloxypropyl Trifluoromethanesulfonate → HCID 19937334, compound

HRID 36588Notes

Reaction equation

HRID 36588 reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:18])([F:17])[CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)(=O)=O.[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:17][C:8]([F:18])([CH2:7][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])[CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1

Participants

4

Reactant 2

HCID 199373062,2-Difluoro-3-Tetrahydropyranyloxypropyl TrifluoromethanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 19937334HCID 19937334, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,2-difluoro-3-tetrahydropyranyloxypropyl trifluoromethanesulfonate (2.3 g, 7 mmol), potassium phthalimide (1.4 g, 7.7 mmol) and anhydrous dimethylformamide (50 ml) under nitrogen was stirred and heated at 85° C. overnight. After cooling, salts are filtered off, and the solvent was removed in uacuo. The residue was taken up in dichloromethane (100 ml), washed with 0.5M NaOH (30 ml) and brine. The organic phase was separated, dried over magnesium sulfate and concentrated. The desired compound 2,2-difluoro-3-phthalimido-1-tetrahydropyranyloxypropane was purified by flash chromatography on silica gel (ethyl acetate:hexane; 20:80) (2 g, 90%).

Workup

  1. temperatureAfter cooling
  2. filtrationsalts are filtered off
  3. customthe solvent was removed in uacuo
  4. washwashed with 0.5M NaOH (30 ml) and brine
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe desired compound 2,2-difluoro-3-phthalimido-1-tetrahydropyranyloxypropane was purified by flash chromatography on silica gel (ethyl acetate:hexane; 20:80) (2 g, 90%)

Sources & evidence

ORD record
ord-9245fec62a834adabef0ee2af378a6c1
Source dataset
uspto-grants-1995_05
Patent number
US05416076

Reaction notes

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