Sodium Hydroxide → HCID 53252926, compound

HRID 1803033Notes

Reaction equation

HRID 1803033 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:26])/[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)=[CH:11][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:26])=[O:5])=[CH:10][CH:11]=2)=[N:18][C:19]([CH3:25])=[C:20]([CH3:24])[N:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56929918HCID 56929918, compound

Product 1

HCID 53252926HCID 53252926, compoundYield 93%

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)-phenyl)acrylic acid ethyl ester (1.0 g, 3.07 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 0.85 g white crystalloid of (E)-3-(4-((3,5,6-Trimethylpyrazin-2-yl)methoxy)-phenyl)acrylic acid, wherein a yield is 93.0%, m.p. 152-154° 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-d3123eb243144a98a1b22f454720e02b
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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