HCID 178519885, compound → HCID 178519884, compound

HRID 1091685Notes

Reaction equation

HRID 1091685 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH2:8][OH:9])=[CH:6][NH:5][N:4]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[F:11][C:2]([F:1])([F:10])[C:3]1[C:7]([CH:8]=[O:9])=[CH:6][NH:5][N:4]=1

Participants

4

Reactant 1

HCID 178519885HCID 178519885, compound

Product 1

HCID 178519884HCID 178519884, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

(3-(Trifluoromethyl)-1H-pyrazol-4-yl)methanol (54.00 g, 0.325 mol) was suspended in toluene (2 L). MnO2 (113.00 g, 1.30 mol) and 4 Å molecular sieve powder (54.00 g) were added. The reaction mixture was stirred at reflux under nitrogen with a Dean-Stark trap for 5.5 h. The resulting mixture was filtered hot and the cake allowed to cool before washing with 1:1 DCM:MeOH solution (3×500 mL). The combined filtrates were concentrated in vacuo to give the desired product (54.00 g, 0.329 mol, 100%).

Workup

  1. temperatureat reflux under nitrogen with a Dean-Stark trap for 5.5 h
  2. filtrationThe resulting mixture was filtered hot
  3. temperatureto cool
  4. washbefore washing with 1:1 DCM
  5. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-2c67a3fd15bc4529bcb698faacad4a89
Source dataset
uspto-grants-2012_03
Patent number
US08129397B2

Reaction notes

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