Methanol → HCID 68484867, compound

HRID 2404574Notes

Reaction equation

HRID 2404574 reaction equation
[C:1]([N:4]1[C:8](=[O:9])[CH2:7][C:6](=[O:10])[N:5]1[C:11]1[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([CH3:23])=[CH:13][C:12]=1[F:24])(=[O:3])[CH3:2].CO.[CH2:27](OCC)C.C[Si](C=[N+]=[N-])(C)C>ClCCl>[C:1]([N:4]1[C:8](=[O:9])[CH:7]=[C:6]([O:10][CH3:27])[N:5]1[C:11]1[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:20])([F:21])[F:22])[C:14]([CH3:23])=[CH:13][C:12]=1[F:24])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 68484704HCID 68484704, compound

Product 1

HCID 68484867HCID 68484867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Then, 1.50 g of 1-acetyl-2-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazolidine-3,5-dione was dissolved in 50 mL of dichloromethane, 5 mL of methanol was added, and 2.1 mL of a diethyl ether solution (2.0 mol/L) of trimethylsilyldiazomethane was added under cooling with ice, followed by stirring at room temperature for 5 hours. Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:2) to obtain 0.69 g of 2-acetyl-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-methoxypyrazol-3-one.

Workup

  1. temperatureunder cooling with ice
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-fd6a0047b78e4049b81898b9951e8033
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

Loading…