Triphenylphosphine → HCID 86644443, compound

HRID 2404517Notes

Reaction equation

HRID 2404517 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N:15]1[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[N:16]1.[F:22][C:23]([F:28])([F:27])[CH2:24][CH2:25]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:12])[F:13])=[CH:4][C:3]=1[N:15]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH2:25][CH2:24][C:23]([F:28])([F:27])[F:22])=[N:16]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 1375123,3,3-Trifluoro-1-propanolHCID 178427864HCID 178427864, compound

Product 1

HCID 86644443HCID 86644443, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.6 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxy-5-methylpyrazole was dissolved in 4 mL of tetrahydrofuran, and 0.23 g of 3,3,3-trifluoropropanol, 0.75 g of triphenylphosphine and 0.71 g of 1,1′-(azodicarbonyl)dipiperidine were added, followed by stirring at room temperature for 12hours. After completion of the reaction, the reaction solution was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (ethyl acetate:hexane=1:4) to obtain 0.61 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-methyl-3-(3,3,3-trifluoropropoxy)pyrazole.

Workup

  1. customAfter completion of the reaction
  2. distillationthe reaction solution was distilled off under reduced pressure
  3. customthe obtained residue was purified by column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-a1a192d6d1ce402ab1b36e5d19e89d36
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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