Glycidol → HCID 43185732, compound

HRID 595010Notes

Reaction equation

HRID 595010 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH2:9]1[O:11][CH:10]1[CH2:12]O.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.C(OCC)(=O)C.O>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:12][CH:10]2[CH2:9][O:11]2)[CH:8]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 11164GlycidolHCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 43185732HCID 43185732, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of 4-nitro-1H-pyrazole (1.0 g, 8.8 mmol), glycidol (0.58 mL, 8.8 mmol) and triphenylphosphine (2.14 g, 10.6 mmol) in THF (40 mL) was added DIAD (2.25 mL, 11.4 mmol). After 24 h the reaction mixture was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed (brine), dried (anhydrous MgSO4) and concentrated. Flash chromatography (Isolera, silica, 50 g, 0-90% ethyl acetate in petroleum ether) afforded 4-nitro-1-(oxiran-2-ylmethyl)-1H-pyrazole as an off-white solid (0.71 g, 48% yield). LCMS (UPLC, low pH), RT=0.74 min.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washthe combined organic layers were washed (brine)
  3. dry with materialdried (anhydrous MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-164786ff434140e9a947975515c40ddd
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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