Iodoethane → Ethyl 2,6-bis(trifluoromethyl)-4-ethoxy-5-methyl-3-pyridinecarboxylate

HRID 542130Notes

Reaction equation

HRID 542130 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+].I[CH2:29][CH3:30]>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][CH2:29][CH3:30])[C:6]([CH3:15])=[C:5]([C:16]([F:19])([F:18])[F:17])[N:4]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469144HCID 178469144, compound

Product 1

HCID 13882898Ethyl 2,6-bis(trifluoromethyl)-4-ethoxy-5-methyl-3-pyridinecarboxylateYield 77.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7.8 g (0.0246 mol) of product of Example 35, 3.5 g of K2CO3, 20 g of iodoethane, and 100 ml of acetone was held at reflux for 2 days and concentrated. The reaction mixture was treated with 150 ml of water and extracted with 200 ml of ether. The ether extract was dried and concentrated. The residual solid (7.5 g) was recrystallized from hexane at low temperature to give 6.6 g (77.7%) of product; mp 72.5°-74° C.

Workup

  1. temperatureat reflux for 2 days
  2. concentrationconcentrated
  3. additionThe reaction mixture was treated with 150 ml of water
  4. extractionextracted with 200 ml of ether
  5. extractionThe ether extract
  6. customwas dried
  7. concentrationconcentrated
  8. customThe residual solid (7.5 g) was recrystallized from hexane at low temperature

Sources & evidence

ORD record
ord-ed90bfa9b6184f019218d6eacc6e66a4
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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