Triphenylphosphine → 4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole

HRID 449882Notes

Reaction equation

HRID 449882 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[O:9]1[CH2:14][CH2:13][CH:12](O)[CH2:11][CH2:10]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:12]2[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 591862964-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazoleYield 175.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

4-nitro-1H-pyrazole (0.15 g, 1.3 mmol), tetrahydro-2H-pyran-4-ol (0.14 g, 1.3 mmol), DIPAD (0.35 g, 1.7 mmol), PPh3 (0.42 g, 1.6 mmol) were dissolved in THF (5 mL) and the resulting mixture was stirred at 25° C. for 3 hours. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography (EtOAc/petroleum ether=6/1) to give 4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (0.45 g). 1H NMR (500 MHz, CDCl3): δ 8.19 (s, 1H), 8.10 (s, 1H), 4.38 (m, 1H), 4.16-4.12 (m, 2H), 3.57-3.53 (m, 2H), 2.17-2.05 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (EtOAc/petroleum ether=6/1)

Sources & evidence

ORD record
ord-9b03d916f3d349108a8b54a22349feec
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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