3,4-dihydro-2H-pyran → HCID 68667915, compound

HRID 1188096Notes

Reaction equation

HRID 1188096 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]2[NH:11][N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=2)=[CH:3][CH:2]=1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1>CC#N.FC(F)(F)C(O)=O>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[N:11]1[C:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:16])=[CH:6][CH:5]=2)=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 178497264HCID 178497264, compound

Product 1

HCID 68667915HCID 68667915, compoundYield 117.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 5-p-tolyl-1H-pyrazole-3-carboxylate (224 mg, 1.03 mmol), 3,4-dihydro-2H-pyran (190 μL, 2.07 mmol) and trifluoroacetic acid (2 μL, 0.02 mmol) in anhydrous MeCN (3 mL) was refluxed for 2 hrs. The solvent was evaporated. The residue was resuspended in CH2Cl2 (50 mL) and was washed with H2O and brine. After drying with Na2SO4, solvent evaporation and silica gel column chromatography (PE-EtOAc, 6:4) methyl 1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazole-3-carboxylate (363 mg, 68%) was obtained.

Workup

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

Sources & evidence

ORD record
ord-cef8b105a0da4a49b3c6be87a4352fb6
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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