Sodium Hydroxide → HCID 25030664, compound

HRID 1803031Notes

Reaction equation

HRID 1803031 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:28])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[C:22]([CH3:23])=[N:21][C:20]([CH3:24])=[C:19]([CH3:25])[N:18]=2)=[C:11]([O:26][CH3:27])[CH:10]=1)C>O>[CH3:23][C:22]1[C:17]([CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9](/[CH:8]=[CH:7]/[C:6]([OH:28])=[O:5])=[CH:10][C:11]=2[O:26][CH3:27])=[N:18][C:19]([CH3:25])=[C:20]([CH3:24])[N:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56929920HCID 56929920, compound

Product 1

HCID 25030664HCID 25030664, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Adding water (20 mL), NaOH (0.14 g, 3.5 mmol) into a 100 mL round-bottom flask, stirring to dissolve, then adding 95% alcohol (20 mL), (E)-3-(4-((3,5,6-Trimethylpyrazin-2-yl) methoxy)-3-methoxyphenyl)acrylic acid ethyl ester (1.0 g, 2.8 mmol), stifling under room temperature to react for 4 hours, TLC [V(petroleum ether):V(ethyl acetate)=3:1 as developing agent] detecting shows that reaction is complete, (Rf of raw material=0.5, Rf of product=0), distilling out the alcohol under reduced pressure, adjusting pH of the reaction solution to 4-5 with 6.0M HCl while keeping the reaction solution cool to separate out solid, filtering, washing the solid with cool water for three times, processing with vacuum filtration, recrystallizing with anhydrous alcohol, drying under 70° C. for 8 hours to obtain 0.87 g white crystalloid of (E)-3-(4-((3,5,6-Trimethylpyrazin-2-yl)methoxy)-3-methoxyphenyl)acrylic acid, wherein a yield is 94.6%, m.p. 156-158° C.

Workup

  1. dissolutionto dissolve
  2. customstifling under room temperature
  3. customto react for 4 hours
  4. distillation(Rf of raw material=0.5, Rf of product=0), distilling out the alcohol under reduced pressure
  5. temperaturecool
  6. customto separate out solid
  7. filtrationfiltering
  8. washwashing the solid with cool water for three times
  9. filtrationprocessing with vacuum filtration
  10. customrecrystallizing with anhydrous alcohol
  11. customdrying under 70° C. for 8 hours

Sources & evidence

ORD record
ord-0b885015fb884c2696344ab0dc87d793
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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