2,2,2-Trifluoroethanol → 3-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 1649691Notes

Reaction equation

HRID 1649691 reaction equation
C1COCC1.[Na].[F:7][C:8]([F:12])([F:11])[CH2:9][OH:10].Cl[C:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([C:24]([Cl:27])([F:26])[F:25])[N:17]=[C:16]([C:28]([F:31])([F:30])[F:29])[C:15]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33]>O>[Cl:27][C:24]([F:25])([F:26])[C:18]1[N:17]=[C:16]([C:28]([F:31])([F:29])[F:30])[C:15]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:14]([O:10][CH2:9][C:8]([F:12])([F:11])[F:7])[C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 8028TetrahydrofuranHCID 5360545Sodium3×HCID 140137593-Ethyl 5-methyl 4-chloro-6-(chlorodifluoromethyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 140137633-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)-3,5-pyridinedicarboxylateYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml of dry THF was added 0.29 g (0.013 mol) of sodium metal. To this mixture 1.28 g (0.013 mol) of 2,2,2-trifluoroethanol was added dropwise. The solution was stirred under N2 until all of the sodium metal had been consumed. Then 5.0 g (0.0126 mol) of product of Example 28 was added to the sodium salt solution and the reaction mixture was allowed to stir at room temperature for 4 hours. The reaction mixture was poured into 100 ml of H2O, and extracted with diethyl ether. The ether phase was dried (MgSO4) and concentrated in vacuo to yield 5.48 g of a gold crystalline solid. This solid was recrystallized in hexane to yield 4.2 g (72.4%) of product as a tan solid; mp 62°-63° C.

Workup

  1. customhad been consumed
  2. extractionextracted with diethyl ether
  3. dry with materialThe ether phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b62fde0f42d4ee2a6ee3c01f4e1d7d2
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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