Lithium Hydroxide → HCID 58503694, compound

HRID 623801Notes

Reaction equation

HRID 623801 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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]=[CH:6][CH:7]=1.C1COCC1.O.[Li+].[OH-]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[CH:11][N:10](/[CH:13]=[CH:14]\[C:15]([OH:17])=[O:16])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 53359060HCID 53359060, compound

Product 1

HCID 58503694HCID 58503694, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 3-neck 100 mL RBF, (Z)-isopropyl 3-(3-(3-chlorophenyl)-1H-1,2,4-triazol-1-yl)acrylate (1.0 g, 1 eq.) was mixed with THF-Water (1:1) (20 mL, 20 Vol.) and LiOH (0.288 g, 2.0 eq.) was added. The reaction mixture was stirred at RT for 2-3 h. Reaction completion was monitored on TLC using neat ethyl acetate as mobile phase. Reaction mixture was quenched into the ice-water slurry (50 mL) and acidified with approximately 5 N HCl to 4 PH. Compound was extracted in the ethylacetate (50 mL×3) and organic layer was washed with brine solution (50 mL×3) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 0.7 g of pure (Z)-3-(3-(3-chlorophenyl)-1H-1,2,4-triazol-1-yl)acrylic acid. Yield (81.8%). LC/MS: 250.0

Workup

  1. additionwas added
  2. customReaction completion
  3. customReaction mixture
  4. customwas quenched into the ice-water slurry (50 mL)
  5. extractionCompound was extracted in the ethylacetate (50 mL×3) and organic layer
  6. washwas washed with brine solution (50 mL×3)
  7. customby drying
  8. concentrationOrganic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ecfcba51abaa4ccb95663599b2864a6b
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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