Dimethyl Sulfate → 3-Methoxy-4,4,4-trifluoro-2-butenoic acid ethyl ester

HRID 1722458Notes

Reaction equation

HRID 1722458 reaction equation
F[C:2](F)(F)C1N(C)N=C(O)C=1.[F:12][C:13]([F:23])([F:22])[C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].S(OC)(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+].COS([O-])(=O)=O.C([N+](CC)(CC)C)C>CC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[CH:15]=[C:14]([O:21][CH3:2])[C:13]([F:22])([F:23])[F:12])[CH3:20]

Participants

7

Reactant 5

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 119903537588-22-9HCID 178481944HCID 178481944, compound

Product 1

HCID 27588673-Methoxy-4,4,4-trifluoro-2-butenoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An alternative method of forming the 5-trifluoromethyl-3-hydroxy-1-methylpyrazole involves reacting ethyl 4,4,4-trifluoroacetoacetate in acetone with dimethyl sulfate in the presence of anhydrous potassium carbonate and preferably triethylmethylammonium methylsulfate to form 3-methoxy-4,4,4-trifluoro-2-butenoic acid ethyl ester. This ester is then reacted directly with methylhydrazine to form the 3- and 5-hydroxy isomer mixture of the pyrazole. The desired isomer can be separated as described above.

Sources & evidence

ORD record
ord-e4bb6bd10484473c96950e42facf3624
Source dataset
uspto-grants-1989_08
Patent number
US04855442

Reaction notes

Loading…