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

HRID 2119423Notes

Reaction equation

HRID 2119423 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-c9c784dd5af542b4ab46acfafce5ad40
Source dataset
uspto-grants-2004_02
Patent number
US06686367B2

Reaction notes

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