Potassium Carbonate → Ethyl 2,6-bis(trifluoromethyl)-4-{4-[(1-ethoxycarbonyl)ethoxy]phenoxy}-3-pyridinecarboxylate

HRID 542125Notes

Reaction equation

HRID 542125 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7](Cl)[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[CH2:21]([O:23][C:24]([CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[O:25])[CH3:22].C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C(C)C>[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][CH2:27][CH2:26][C:24]([O:23][CH2:21][CH3:22])=[O:25])=[CH:30][CH:31]=2)[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl esterHCID 216663104-[(1-Ethoxycarbonyl)ethoxy]phenol

Product 1

HCID 86741396Ethyl 2,6-bis(trifluoromethyl)-4-{4-[(1-ethoxycarbonyl)ethoxy]phenoxy}-3-pyridinecarboxylateYield 68.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A 250 ml round bottom flask is charged with 3.54 g (0.011 mol) of product of Example 19, 2.31 g (0.011 mol) of 4-[(1-ethoxycarbonyl)ethoxy]phenol and 1.82 g (0.013 mol) of K2CO3 in 150 ml of methyl isobutyl ketone. This mixture was stirred at reflux for 18 hours, filtered and concentrated. The residue was taken up in ether, washed with 5% NaOH, water, dried (MgSO4) and concentrated in vacuo to afford 3.75 g of an orange oil. Purification by HPLC using 18% ethyl acetate/cyclohexane as eluting solvent gave 2.66 g of an oil which was kugelrohr distilled at 41 Pa, pot temperature 150°-154° C., affording 2.56 g (47.0%) of product as a clear oil, nD25 1.4732.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washwashed with 5% NaOH, water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-570251edfcb74491bbd5d30df98d8544
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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