Trifluoroacetic acid → HCID 59408782, compound

HRID 1188142Notes

Reaction equation

HRID 1188142 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=1)([O-:3])=[O:2].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.FC(F)(F)C(O)=O>CC#N>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[N:8]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 80803,4-dihydro-2H-pyranHCID 135452337methyl 3-nitro-1H-pyrazole-5-carboxylate

Product 1

HCID 59408782HCID 59408782, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 5-nitro-1H-pyrazole-3-carboxylate (7.5 g, 43.8 mmol), 3,4-dihydro-2H-pyran (8 mL, 87.7 mmol) and trifluoroacetic acid (65 μL, 0.9 mmol) in anhydrous MeCN (100 mL) was refluxed for 16 hrs. The solvent was evaporated and the residue was resuspended in CH2Cl2 (50 mL) and washed with H2O and brine. After drying with Na2SO4, solvent evaporation and silica gel column chromatography (PE-EtOAc, 9:1) methyl 1-(tetrahydro-2H-pyran-2-yl)-5-nitro-1H-pyrazole-3-carboxylate (3.71 mg, 33%) was obtained.

Workup

  1. temperaturewas refluxed for 16 hrs
  2. customThe solvent was evaporated
  3. washwashed with H2O and brine
  4. dry with materialAfter drying with Na2SO4, solvent evaporation

Sources & evidence

ORD record
ord-225b50fdfc4c4380b667bd43397495fb
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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