Isopropyl iodide → Ethyl 2,6-bis(trifluoromethyl)-4-isopropoxy-5-methyl-3-pyridinecarboxylate

HRID 542131Notes

Reaction equation

HRID 542131 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:14])[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH:28](I)([CH3:30])[CH3:29]>CC(C)=O>[F:21][C:2]([F:20])([F:1])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH:28]([CH3:30])[CH3:29])[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178469144HCID 178469144, compound

Product 1

HCID 13882899Ethyl 2,6-bis(trifluoromethyl)-4-isopropoxy-5-methyl-3-pyridinecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 15.1 g (0.209 mol) of product of Example 35, 6.6 g (0.2 mol) of potassium carbonate, 32 g of isopropyl iodide and 50 ml of acetone was held at reflux for 18 hours and concentrated. The residue was treated with water and filtered. The solid was dissolved in ether (100 ml) and the ether solution was washed with 50 ml of 10% NaOH, dried, and concentrated. The residue was recrystallized from hexane to give 14.2 g (83%) of product; mp 53°-55° C.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated
  3. additionThe residue was treated with water
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in ether (100 ml)
  6. washthe ether solution was washed with 50 ml of 10% NaOH
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-7fa15f53df234553a9ce781bdd8dd9c3
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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