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

HRID 857703Notes

Reaction equation

HRID 857703 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.FC(F)(F)C(O)=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 4

HCID 1048PyrazoleHCID 6422Trifluoroacetic acidHCID 80803,4-dihydro-2H-pyranHCID 24758Sodium hydride

Product 1

HCID 218663101-(2-Tetrahydropyranyl)-1H-pyrazole

Procedure

To pyrazole (14.3 g, 0.21 mol) was added 3,4-dihydro-2H-pyran (29 ml, 0.315 mol) and, after complete dissolving, trifluoroacetic acid (0.1 ml, 0.0013 mol) was added to the obtained solution. The reaction mixture was refluxed for 5 h, sodium hydride (0.2 g, 0.008 mol) was added, and the mixture was distilled to give 1-(tetrahydro-pyran-2-yl)1H-pyrazole; b.p. ˜60–65° C./0.5–1 torr.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. distillationthe mixture was distilled

Sources & evidence

ORD record
ord-8edd78f0924d45ef8c2f7c91b2ba721a
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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