Lithium Hydroxide → HCID 86672064, compound

HRID 623820Notes

Reaction equation

HRID 623820 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][N:10](/[CH:13]=[CH:14]\[C:15]([O:17]C(C)C)=[O:16])[N:9]=2)[CH:5]=[C:4]([O:21][CH:22]([CH3:24])[CH3:23])[N:3]=1.[Li+].[OH-].C(OCC)(=O)C>C1COCC1.O.CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][N:10](/[CH:13]=[CH:14]\[C:15]([OH:17])=[O:16])[N:9]=2)[CH:5]=[C:4]([O:21][CH:22]([CH3:24])[CH3:23])[N:3]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 58503800HCID 58503800, compound

Product 1

HCID 86672064HCID 86672064, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

In a 250-mL, 2-neck round-bottomed flask equipped with rubber septum, (Z)-isopropyl 3-(3-(2-chloro-6-isopropoxypyridin-4-yl)-1H-1,2,4-triazol-1-yl)acrylate (2.0 g, 1.0 eq.) was dissolved in THF:Water (1:1) (20 mL: 20 mL). To this reaction mixture LiOH (0.478 g, 2 eq.) was added and reaction mixture was stirred at room temperature to 2-3 h. 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 water (500 mL) and acidified using dilute HCl. The aqueous layer was extracted multiple times with ethyl acetate (100 mL×3). The organic layer were washed with saturated brine solution and dried over anhydrous NaSO4. The organic layer was concentrated under reduced pressure to obtain 1.61 g (91.7%) of desired compound.

Workup

  1. customreaction mixture
  2. customReaction mixture
  3. customwas quenched in water (500 mL)
  4. extractionThe aqueous layer was extracted multiple times with ethyl acetate (100 mL×3)
  5. washThe organic layer were washed with saturated brine solution
  6. dry with materialdried over anhydrous NaSO4
  7. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88f403cd1b8a4421978b1dd9eedef788
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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