Butyl iodide → 4,6-Dibutoxy-2-trifluoromethylpyridine-3-carboxylic acid ethyl ester

HRID 1251950Notes

Reaction equation

HRID 1251950 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18](I)[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH2:7][CH2:2][CH2:3][CH3:4])[N:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 178470040HCID 178470040, compound

Product 1

HCID 137267874,6-Dibutoxy-2-trifluoromethylpyridine-3-carboxylic acid ethyl esterYield 198.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mechanically stirred mixture of 22.6 g (0.09 mol) of product of Example 1, 99 g of butyl iodide, 24.84 g of potassium carbonate and 250 ml of acetone was held at reflux for 26 hours and filtered. The acetone filtrate was concentrated and the residue was dissolved in ether. The ether solution was washed with water, dried, and concentrated. The residue was kugelrohr distilled at 0.3 torr to give 32.5 g (99%) of product, nD25 1.4543.

Workup

  1. temperatureat reflux for 26 hours
  2. filtrationfiltered
  3. concentrationThe acetone filtrate was concentrated
  4. dissolutionthe residue was dissolved in ether
  5. washThe ether solution was washed with water
  6. customdried
  7. concentrationconcentrated
  8. distillationThe residue was kugelrohr distilled at 0.3 torr

Sources & evidence

ORD record
ord-becb1e6e299d4f4dacf779ec6e58188c
Source dataset
uspto-grants-1988_05
Patent number
US04741766

Reaction notes

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