3-Furanol, tetrahydro- → HCID 86679660, compound

HRID 577714Notes

Reaction equation

HRID 577714 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].O[CH:10]1[CH2:14][CH2:13][O:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 99603-Furanol, tetrahydro-HCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 86679660HCID 86679660, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitropyrazole (1 g, 8.8 mmol), 3-hydroxy-tetrahydrofuran (779 mg, 8.8 mmol) and triphenylphosphine (2.81 g, 10.56 mmol) in THF (30 mL) at 0° C. was added diisopropylazodicarboxylate (2.27 g, 1 mmol) dropwise and the reaction was allowed to warm to rt overnight. The reaction was concentrated and purified on SiO2 (30% EtOAc/heptane) to give 4-nitro-1-(tetrahydrofuran-3-yl)-1H-pyrazole as a clear oil. The oil was then dissolved in EtOH (30 mL) and hydrogenated via H-cube with 10% Pd/C at 30 psi H2 for 3 hrs. The solvent was removed and the residue was purified on SiO2 (1%-10% EtOH/EtOAc) to give the title compound (1.0 g, 42% yield) as an orange oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.10-2.21 (m, 1H), 2.22-2.35 (m, 1H), 3.72-3.85 (m, 4H), 3.85-3.96 (m, 2H), 4.76-4.85 (m, 1H), 6.93 (s, 1H), 7.05 (s, 1H). m/z (APCI+) for C7H11N3O 154.1 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified on SiO2 (30% EtOAc/heptane)

Sources & evidence

ORD record
ord-989e42f84c5f43fd924c7e1235738ec7
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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