Acetic Acid → 4-Chloro-3,5-difluoro-2-(1-hydroxy-2-propyl)pyridine

HRID 1080214Notes

Reaction equation

HRID 1080214 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([CH:9]([CH3:18])[CH2:10][O:11]C2CCCCO2)[C:3]=1[F:19].O.C(O)(=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([CH:9]([CH3:18])[CH2:10][OH:11])[C:3]=1[F:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 540115134-Chloro-3,5-difluoro-2-(1-(2-tetrahydropyranyl)oxy-2-propyl)pyridine

Product 1

HCID 543283394-Chloro-3,5-difluoro-2-(1-hydroxy-2-propyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

The product of Step 1 is dissolved in 200 mL of 2:1 THF:water and to this solution is added 6 mL of acetic acid. The reaction mixture is heated at 45° C. for approximately 5 hours. The THF is removed under reduced pressure and the aqueous reaction mixture is adjusted to a pH in the range of 8 to 9 with 10% sodium carbonate and is then extracted with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound.

Workup

  1. customThe THF is removed under reduced pressure
  2. extractionis then extracted with methylene chloride
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22d870fc6965446d8037cd85e3adeaac
Source dataset
uspto-grants-1996_12
Patent number
US05580872

Reaction notes

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