Ethanol → Diethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:15][CH3:16])[C:6]([C:17]([OH:19])=[O:18])=[C:5]([C:20]([F:23])([F:22])[F:21])[N:4]=1.S(Cl)(Cl)=O.[CH2:30](O)[CH3:31]>>[F:25][C:2]([F:24])([F:1])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:15][CH3:16])[C:6]([C:17]([O:19][CH2:30][CH3:31])=[O:18])=[C:5]([C:20]([F:22])([F:21])[F:23])[N:4]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 140137533-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate2×

Product 1

HCID 14013779Diethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate

Procedure

This material was obtained from product of Example 14 and ethanol according to the following general procedure: A 5.0 g portion of the acid product of Example 14 was refluxed with excess thionyl chloride until the reaction was completed. Excess thionyl chloride was removed in vacuo. The residual acid chloride was refluxed with an excess of appropriate alcohol (ethanol in this Example) for 2-4 hours and concentrated to give the desired product. The crude product was purified by a wash with 20% K2CO3 and isolated as a solid (20.3% yield), mp 28°-30° C.