Lithium Hydroxide → HCID 86672061, compound

HRID 623812Notes

Reaction equation

HRID 623812 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][CH3:22])[N:3]=1.[OH-].[Li+].CCOC(C)=O.CCCCCC>C1COCC1>[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][CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21226206Ethyl acetate hexaneHCID 53386232HCID 53386232, compound

Product 1

HCID 86672061HCID 86672061, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 25-mL, 3N round-bottomed flask equipped with Thermometer pocket and rubber septum, (Z)-isopropyl 3-(3-(2-chloro-6-methoxypyridin-4-yl)-1H-1,2,4-triazol-1-yl)acrylate (0.7 g, 1.0 eq.) dissolve in THF (4 ml) was added lithium hydroxide (0.182 g, 2.0 eq.) (dissolved in water), resulting reaction mixture was stir at RT. The progress of the reaction was followed by TLC analysis on silica gel with 20% EtOAc-hexane as mobile phase which shows that starting material was consumed after 5 h. THF was removed under reduce pressure, aqueous layer washed with ethyl acetate then acidified to 3-5 pH and extract by ethyl acetate (30 ml×3), combined organic layer were dried over sodium sulfate and concentrate under reduce pressure to obtain crude material (0.228 g), crude material was subjected to column purification. The crude compound was purified by column chromatography using 60/120 silica gel and ethyl acetate in hexane as mobile phase. The column was packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection. The compound started eluting from 10% ethyl acetate in hexane. Fractions containing such TLC profile were collected together to obtain pure compound 0.180 g yield (29.97%); LCMS (%): 93.46% [M+H]+ 280.81 RT: 3.213 min.

Workup

  1. customresulting
  2. customreaction mixture
  3. customwas consumed after 5 h
  4. customTHF was removed
  5. washwashed with ethyl acetate
  6. extractionextract by ethyl acetate (30 ml×3)
  7. dry with materialwere dried over sodium sulfate
  8. concentrationconcentrate
  9. customto obtain crude material (0.228 g), crude material
  10. customwas subjected to column purification
  11. customThe crude compound was purified by column chromatography
  12. washstarted eluting in ethyl acetate in gradient manner
  13. customstarting with fraction collection
  14. washThe compound started eluting from 10% ethyl acetate in hexane
  15. additionFractions containing such TLC profile
  16. customwere collected together

Sources & evidence

ORD record
ord-1098a1ca9cbc4a9084f510aafc60cf06
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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