2,2,3,3-Tetrafluoro-1-propanol → HCID 58042517, compound

HRID 2048085Notes

Reaction equation

HRID 2048085 reaction equation
[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][OH:4].[H-].[Na+].Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=1>C1COCC1>[Cl:18][C:17]1[C:12]([O:4][CH2:3][C:2]([F:8])([F:1])[CH:5]([F:7])[F:6])=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 169882,3-DichloropyridineHCID 24758Sodium hydride

Product 1

HCID 58042517HCID 58042517, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2,3,3-Tetrafluoropropan-1-ol (60.0 g, 0.45 mol) was added to a slurry of NaH (60% dispersion in oil, 15.20 g, 0.63 mol) in anhydrous THF (450 mL) at 0° C. and the reaction mixture allowed to warm up to room temperature, then stirred for 1 hour. 2,3-dichloropyridine (45.0 g, 0.30 mol) was added and the reaction heated to a gentle reflux for 16 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The residue was partitioned between EtOAc (300 mL) and brine (200 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to afford the title compound as a yellow oil (71 g, 96%):

Workup

  1. temperaturethe reaction heated to
  2. temperaturea gentle reflux for 16 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent removed in vacuo
  5. customThe residue was partitioned between EtOAc (300 mL) and brine (200 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-33fdbd8774a24f75a84a191e50da58b1
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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