Acetic Acid → 5-Ethyl-2-[(6-fluoropyridin-2-yl)oxy]phenyl acetate

HRID 1023932Notes

Reaction equation

HRID 1023932 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=2)=[C:7]([OH:9])[CH:8]=1)[CH3:2].C(N(CC)CC)C.[C:25](O)(=[O:27])[CH3:26]>CN(C)C=O>[C:25]([O:9][C:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=[CH:5][C:6]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 167527195-Ethyl-2-[(6-fluoropyridin-2-yl)oxy]phenol

Product 1

HCID 591913255-Ethyl-2-[(6-fluoropyridin-2-yl)oxy]phenyl acetateYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Ethyl-2-(6-fluoro-pyridin-2-yloxy)-phenol (20 mg; 0.09 mmol), under argon, in dimethylformamide (2 mL), cooled to 0° C., was added triethylamine (36 μL; 0.26 mmol) and acetic acid (10 μL; 0.18 mmol). The reaction mixture was allowed to stir overnight, with gradual warming to roomtemperature. The reaction was concentrated, diluted with saturated NaHCO3 (5 mL) and extracted with ethyl acetate (3*3 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo, the title compound (8 mg; 34%) was obtained as clear oil, after purification on neutral alumina gel (cyclohexane/ethyl acetate: 9/1).

Workup

  1. temperaturewith gradual warming to roomtemperature
  2. concentrationThe reaction was concentrated
  3. additiondiluted with saturated NaHCO3 (5 mL)
  4. extractionextracted with ethyl acetate (3*3 mL)
  5. dry with materialCombined organic phases were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6bf22fe711754776a2771ef719bf4cda
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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