4,4,4-Trifluoro-1-phenyl-1,3-butanedione → 2-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanol

HRID 891063Notes

Reaction equation

HRID 891063 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1)[NH2:3].[C:13]([CH2:21][C:22](=O)[C:23]([F:26])([F:25])[F:24])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([C:13]2[N:2]([C:4]3[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][OH:12])=[CH:8][CH:9]=3)[N:3]=[C:22]([C:23]([F:24])([F:25])[F:26])[CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 222447112-(4-Hydrazinophenyl)ethanol hydrochloride

Product 1

HCID 222445582-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanolYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-hydrazinophenyl)ethanol hydrochloride (J. Med. Chem., 1999, 42, 2504, 202 mg, 1.07 mmol) and benzoyl-1,1,1-trifluoroacetone (278 mg, 1.28 mmol) in ethanol (13 mL) was heated under reflux overnight. After removal of the solvent, the resulting residue was partitioned between dichloromethane and water. Organic phase was washed with brine and dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 200 mg (56%) of the title compound as yellow solids: MS (ESI) m/z 333 [M+H]+, 1H-NMR (CDCl3) δ 7.36-7.20 (9H, m), 6.74 (1H, s), 3.86 (2H, br.s), 2.89 (2H, t, J=6.6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customAfter removal of the solvent
  4. customthe resulting residue was partitioned between dichloromethane and water
  5. washOrganic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customAfter removal of the solvent
  8. customthe crude product was purified by TLC with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-9e07c64372314e6692139765531f2263
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

Loading…