Acetone → Ethyl 4,6-diisopropoxy-2-(trifluoromethyl)-3-pyridinecarboxylate

HRID 1251951Notes

Reaction equation

HRID 1251951 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].C(=O)([O-])[O-].[K+].[K+].I[CH:25]([CH3:27])[CH3:26].[CH3:28][C:29]([CH3:31])=O>>[CH:25]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH:29]([CH3:31])[CH3:28])[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])([CH3:27])[CH3:26]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178470040HCID 178470040, compound

Product 1

HCID 13726788Ethyl 4,6-diisopropoxy-2-(trifluoromethyl)-3-pyridinecarboxylateYield 98%

Procedure

A mixture of 37.3 g of product of Example 1, 41 g of potassium carbonate, 99 g of 2-iodopropane and 300 ml of acetone was held at reflux for 21 hours. The reaction mixture was filtered. The acetone filtrate was concentrated. The residue was taken into ether and the ether solution was washed with 10% sodium hydroxide, dried, and concentrated. The residue was kugelrohr distilled to give 48.8 g (98%) of product, nD25 1.4491.

Workup

  1. temperatureat reflux for 21 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe acetone filtrate was concentrated
  4. washthe ether solution was washed with 10% sodium hydroxide
  5. customdried
  6. concentrationconcentrated
  7. distillationThe residue was kugelrohr distilled

Sources & evidence

ORD record
ord-da863c1feb624a07a9c7094d305ea8db
Source dataset
uspto-grants-1988_05
Patent number
US04741766

Reaction notes

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