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

HRID 1843097Notes

Reaction equation

HRID 1843097 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([C:12]([F:15])([F:14])[F:13])[C:4]([C:16](OCC)=[O:17])=[N:3]1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.C1CCCCC1>[OH:17][CH2:16][C:4]1[C:5]([C:12]([F:13])([F:14])[F:15])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 67379138diethyl 1-methyl-4-(trifluoromethyl)-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 58542528ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

A solution of 6.00 g (20.4 mmol) of diethyl 1-methyl-4-(trifluoromethyl)-1H-pyrazole-3,5-dicarboxylate in 80 ml of tetrahydrofuran is admixed under argon at −78° C. with 38.9 ml (42.8 mmol) of a 1.1M solution of diisobutylaluminium hydride in cyclohexane and stirred overnight at this temperature. The reaction mixture is admixed with water and extracted twice with ethyl acetate. The organic phase is dried over sodium sulphate, filtered over silica gel and concentrated by evaporation in vacuo. Chromatographic purification on silica gel gives 4.10 g of ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (80%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered over silica gel
  4. concentrationconcentrated by evaporation in vacuo
  5. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-5fa13397378c4071a440bce441394cdc
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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