Methyl iodide → Methyl 4-methoxy-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate

HRID 414020Notes

Reaction equation

HRID 414020 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[F:9][C:10]([F:27])([F:26])[C:11]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([OH:21])[CH:14]=[C:13]([C:22]([F:25])([F:24])[F:23])[N:12]=1>CC(C)=O>[CH3:3][O:21][C:15]1[CH:14]=[C:13]([C:22]([F:25])([F:24])[F:23])[N:12]=[C:11]([C:10]([F:26])([F:9])[F:27])[C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178498966Methyl 2,6-bis(trifluoromethyl)-4-hydroxy-3-pyridinecarboxylate

Product 1

HCID 13882874Methyl 4-methoxy-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl iodide (32.3 ml, 0.519 mol), potassium carbonate (14.4 g, 0.104 mol), and product of Step 2 (25.0 g, 0.086, 5 mol) in acetone (100 ml) was refluxed for 18 hours and concentrated. The residue was dissolved in ether and washed with water. The ether layer was worked up as usual. The crude product, a yellow solid (27.25 g), was recrystallized (chloroform petroleum ether) to afford white rods (22.95 g), yield--88%; mp 101°-103° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with water
  5. customThe crude product, a yellow solid (27.25 g), was recrystallized (chloroform petroleum ether)
  6. customto afford white rods (22.95 g)
  7. customyield--88%

Sources & evidence

ORD record
ord-c20917e14d6f41a38256fc2fd1f50c9e
Source dataset
uspto-grants-1988_12
Patent number
US04789395

Reaction notes

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