Sodium hydride → HCID 178526672, compound

HRID 1289837Notes

Reaction equation

HRID 1289837 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][N:11]=[C:12]([C:19]([F:22])([F:21])[F:20])[CH2:13][C:14](OCC)=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([OH:15])=[CH:13][C:12]([C:19]([F:22])([F:21])[F:20])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 2738115Ethyl trifluoroacetoacetate 4-nitrophenylhydrazone

Product 1

HCID 178526672HCID 178526672, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 382 mg (1.2 mmol) of ethyl trifluoroacetoacetate 4-nitrophenylhydrazone in 10 ml of THF was added 53 mg (60%; 1.32 mmol) of NaH and the resulting mixture was stirred at room temperature for 4 hours and at 50° C. for 16 hours. The reaction mixture was quenched with ammonium chloride solution, the aqueous layer was extracted with ethyl acetate (3×), and the combined organic layer was dried and concentrated in vacuo. The residue was purified by column chromatography (silica gel; 50% ethyl acetate in hexane) and recrystallized from methylene chloride/hexane to afford 1-(4-nitrophenyl)-3-trifluoromethyl-5-hydroxypyrazole as a white solid.

Workup

  1. customThe reaction mixture was quenched with ammonium chloride solution
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  3. customthe combined organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel; 50% ethyl acetate in hexane)
  6. customrecrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-1e1d1efa4c5d42c19763fdedab9c9907
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

Loading…