Sodium hydride → HCID 58465096, compound

HRID 1185312Notes

Reaction equation

HRID 1185312 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]1.[H-].[Na+]>CN(C=O)C>[CH3:7][N:6]1[C:2]([O:18][CH2:17][CH:14]2[CH2:15][CH2:16][O:11][CH2:12][CH2:13]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazole

Product 1

HCID 58465096HCID 58465096, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-1-methyl-4-nitro-1H-pyrazole (0.2 g, 1.24 mmol) and tetrahydro-2H-pyran-4-yl-methanol (0.223 g, 1.92 mmol) in DMF (20 mL) cooled to 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.128 g, 3.2 mmol) portionwise. The mixture was warmed to room temperature and stirred for 1 hr. The mixture was concentrated under reduced pressure and the residue dissolved in EtOAc. The organic layer was washed with water, separated and passed through a phase separator cartridge. The solvent was removed under reduced pressure and the crude product was purified via silica gel column chromatography (0-80% EtOAc/isohexane) to give 1-methyl-4-nitro-5-((tetrahydro-2H-pyran-4-yl)methoxy)-1H-pyrazole as a clear oil (143 mg, 48%). 1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 4.28 (d, J=6.3 Hz, 2H), 4.07-3.96 (m, 4H), 3.71 (s, 3H), 2.22-2.09 (m, 1H), 1.82-1.62 (m, 4H)

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic layer was washed with water
  4. customseparated
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified via silica gel column chromatography (0-80% EtOAc/isohexane)

Sources & evidence

ORD record
ord-c098d0b9fbe24e3bbde4de0e00983d32
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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