Hydrazine hydrate (1:1) → 5-Furyl-3-trifluoromethyl-3-hydroxypyrazoline

HRID 649826Notes

Reaction equation

HRID 649826 reaction equation
C(C1C=CC=CC=1[N:9]1[C:13]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)=[CH:12][C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]1)#N.FC(F)(F)C(=O)CC(C1OC=CC=1)=[O:28].O.NN>C(O)C>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[CH:13]1[NH:9][NH:10][C:11]([C:19]([F:22])([F:21])[F:20])([OH:28])[CH2:12]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 185497871-(2-Cyanophenyl)-5-furyl-3-trifluoromethylpyrazole

Product 1

HCID 700273515-Furyl-3-trifluoromethyl-3-hydroxypyrazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part B: 1-(2-cyanophenyl)-5-furyl-3-trifluoromethylpyrazole: To a solution of 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione (2.06 g, 10 mmol) in ethanol (mL) was added hydrazine monohydrate (0.46 g, 10 mmol). The resulting mixture was refluxed for 16 hours and dried under vacuum to give 5-furyl-3-trifluoromethyl-3-hydroxypyrazoline in almost quantitative yield. 1H NMR (CDCl3) δ7.48 (d, J=1.9 Hz, 1H), 6.63 (d, J=3.7 Hz, 1H), 6.47 (dd, J=3.7 Hz, J=1.9 Hz, 1H), 6.16 (s, 1H), 3.48 (d, J=17.9 Hz, 1H), 3.18 (d, J=17.9 Hz, 1H); 19F NMR (CDCl3): δ−81.47; ESMS(+): 221 (M+H, 100).

Workup

  1. temperatureThe resulting mixture was refluxed for 16 hours
  2. customdried under vacuum

Sources & evidence

ORD record
ord-33f4a5ae82b7400d940987702d6a55a0
Source dataset
uspto-grants-2001_08
Patent number
US06271237B1

Reaction notes

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