Lithium Hydroxide → HCID 70556464, compound

HRID 623822Notes

Reaction equation

HRID 623822 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([O:22]C(C)C)=[O:21])[N:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.[Li+].[OH-].C(OCC)(=O)C>C1COCC1.O.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([OH:22])=[O:21])[N:14]=2)[CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 58503679HCID 58503679, compound

Product 1

HCID 70556464HCID 70556464, compoundYield 93.23%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In a 100 mL, 3-neck round-bottomed flask equipped with nitrogen inlet, and a rubber septum, (Z)-isopropyl 3-(3-(3-chloro-5-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-1-yl)acrylate (0.750 g, 1.0 eq.) was dissolved in THF (30 mL, 40 V) and H2O (30 mL, 40 V). The reaction mixture was added LiOH (0.419 g, 5 eq.). The reaction mixture was stirred at room temperature. The progress of the reaction was followed by TLC analysis on silica gel with 20% ethyl acetate in hexane as mobile phase. Reaction mixture was Quenched in 500 ml water and made acidic by dilute HCl. The aqueous layer was extracted with ethyl acetate. The organic layer were washed with Brine solution, dried over NaSO4 and distilled under reduce pressure to obtain 0.620 g (93.23%) crude material.

Workup

  1. customIn a 100 mL, 3-neck round-bottomed flask equipped with nitrogen inlet
  2. customReaction mixture
  3. customwas Quenched in 500 ml water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe organic layer were washed with Brine solution
  6. dry with materialdried over NaSO4
  7. distillationdistilled

Sources & evidence

ORD record
ord-b394d02dd71340d49ed8e2871167e5fc
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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