Allyl bromide → HCID 86713806, compound

HRID 521858Notes

Reaction equation

HRID 521858 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]([CH2:10][CH:11]=[CH2:12])[CH2:8][OH:9])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=[N:3]1.[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([O:9][CH2:8][CH:7]([C:6]1[N:2]([CH3:1])[N:3]=[CH:4][C:5]=1[N+:13]([O-:15])=[O:14])[CH2:10][CH:11]=[CH2:12])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 86713807HCID 86713807, compound

Product 1

HCID 86713806HCID 86713806, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(2-methyl-4-nitro-pyrazol-3-yl)pent-4-en-1-ol (91 mg, 0.43) in anhydrous DMF (5 mL) was added at 0° C. sodium hydride (20 mg, 0.49 mmol, 60 mass %). After stirring at 0° C. for 15 min, allyl bromide (79, 0.64 mmol) was added slowly, stirred at 0° C. for 10 min then warm to room temperature for 2 h. The reaction was quenched with water (10 ml) and extracted with EA (3×50 ml). Combined organic layer was washed with brine (10 ml) and concentrated to dryness. The residue was purified via silica gel chromatography (0-100% EtOAc/heptane) to afford 5-[1-(allyloxymethyl)but-3-enyl]-1-methyl-4-nitro-pyrazole (84 mg, 78%).

Workup

  1. stirringstirred at 0° C. for 10 min
  2. temperaturethen warm to room temperature for 2 h
  3. customThe reaction was quenched with water (10 ml)
  4. extractionextracted with EA (3×50 ml)
  5. washCombined organic layer was washed with brine (10 ml)
  6. concentrationconcentrated to dryness
  7. customThe residue was purified via silica gel chromatography (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-65f7cfa927ea4c38875b59ceb4cb3b44
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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