Pyrazole → 1-(2-Tetrahydropyranyl)-1H-pyrazole

HRID 605911Notes

Reaction equation

HRID 605911 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1>C(O)(C(F)(F)F)=O.[H-].[Na+]>[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 1048PyrazoleHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 218663101-(2-Tetrahydropyranyl)-1H-pyrazoleYield 104.2%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 24758Sodium hydrideCatalyst

Conditions

Temperature
95 °C

Procedure

1H-Pyrazole (14.3 g, 0.21 mol) is dissolved in 3,4-dihydro-2H-pyran (26.74 g, 0.32 mol) in the presence of a catalytic amount of TFA (0.1 mL, 1.3 mmol). The reaction mixture is stirred at 95° C. for 5 hours, cooled and then quenched using NaH (0.2 g, 5 mmol). The solvent is removed to give the title compound as a brown oil (33.3 g, 99%), which is used in the next step without further purification.

Workup

  1. temperaturecooled
  2. customquenched
  3. customThe solvent is removed

Sources & evidence

ORD record
ord-530cac414cee4a89b9338131386ae2f9
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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