Potassium Hydroxide → 6-((Tetrahydro-2H-pyran-4-yl)methoxy)-5-(trifluoromethyl)picolinic acid

HRID 632285

Reaction equation

HRID 632285 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[OH-].[K+].[O:17]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]1>CS(C)=O>[O:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:24][C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2773573(Oxan-4-yl)methanolHCID 707010166-Chloro-5-(trifluoromethyl)picolinic acid

Product 1

HCID 710873886-((Tetrahydro-2H-pyran-4-yl)methoxy)-5-(trifluoromethyl)picolinic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Chloro-5-(trifluoromethyl)picolinic acid (330 mg, 1.46 mmol) and powdered potassium hydroxide (328 mg, 5.85 mmol) were dissolved in DMSO (9 mL). The solution was stirred for 15 min. at ambient temperature. (Tetrahydro-2H-pyran-4-yl)methanol (170 mg, 170 μL, 1.46 mmol; CAN 14774-37-9) was added. The mixture was stirred for 1 d at ambient temp., poured onto ice water/brine/1N HCl (75 mL) and extracted with EtOAc (2×150 mL). The combined extracts were washed with ice water/brine (75 mL), dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound as a grey solid (385 mg, 86%) which was used in the next step without further purification. MS: 304.0 [M−H]−.

Workup

  1. stirringThe mixture was stirred for 1 d at ambient temp.
  2. additionpoured onto ice water/brine/1N HCl (75 mL)
  3. extractionextracted with EtOAc (2×150 mL)
  4. washThe combined extracts were washed with ice water/brine (75 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ed82bb8ba16a4b558e0b9e9a5bd2b406
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Linked notes

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