Solketal → 2,3,5,6-Tetrafluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridine

HRID 2297627Notes

Reaction equation

HRID 2297627 reaction equation
[F:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([F:9])=[C:4](F)[C:3]=1[F:11].[CH3:12][C:13]1([CH3:20])[O:17][CH:16]([CH2:18][OH:19])[CH2:15][O:14]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[F:8][C:6]1[C:5]([F:9])=[C:4]([O:19][CH2:18][CH:16]2[CH2:15][O:14][C:13]([CH3:20])([CH3:12])[O:17]2)[C:3]([F:11])=[C:2]([F:1])[N:7]=1

Participants

5

Reactant 3

HCID 7528SolketalHCID 10796Cesium carbonateHCID 69690Pentafluoropyridine

Product 1

HCID 234422212,3,5,6-Tetrafluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridineYield 94.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To pentafluoropyridine (2.0 g, 12 mmol) dissolved in DMSO was added 2,2-dimethyl-1,3-dioxolane-4-methanol (solketal) (1.5 mL, 12 mmol) and Cs2CO3 (3.8 g, 12 mmol). The slurry was heated in an oil bath at 60° C. for 1 day. The reaction was partitioned with water and ethyl acetate, washed with water and brine, dried (Na2SO4) and the solvent was removed to give 2,3,5,6-tetrafluoro-4-[[(2,2-dimethyl)dioxolan-4-yl]methoxy]pyridine (3.2 g).

Workup

  1. customThe reaction was partitioned with water and ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-2f29f8499da54fd0b3c1bc055a065af1
Source dataset
uspto-grants-2002_12
Patent number
US06492376B2

Reaction notes

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