ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate → ethyl 3-formyl-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate

HRID 1843098Notes

Reaction equation

HRID 1843098 reaction equation
[OH:1][CH2:2][C:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]([CH3:17])[N:4]=1>ClCCl.[O-2].[Mn+4].[O-2]>[CH:2]([C:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]([CH3:17])[N:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 58542528ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 58542586ethyl 3-formyl-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.50 g (5.95 mmol) of ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate in 100 ml of dichloromethane is admixed with 4.14 g (47.6 mmol) of manganese(IV) oxide and heated under reflux for four hours. The cooled reaction mixture is filtered over Celite and concentrated by evaporation on a rotary evaporator. This gives 1.36 g of ethyl 3-formyl-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (91%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for four hours
  3. customThe cooled reaction mixture
  4. filtrationis filtered over Celite
  5. concentrationconcentrated by evaporation on a rotary evaporator

Sources & evidence

ORD record
ord-2089c3208dc5482186d58c531b0c7723
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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