Dimethylformamide → HCID 56929920, compound

HRID 1803030Notes

Reaction equation

HRID 1803030 reaction equation
Br[CH2:2][C:3]1[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=1.[CH2:12]([O:14][C:15](=[O:27])/[CH:16]=[CH:17]/[C:18]1[CH:26]=[CH:25][C:23]([OH:24])=[C:20]([O:21][CH3:22])[CH:19]=1)[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:12]([O:14][C:15](=[O:27])/[CH:16]=[CH:17]/[C:18]1[CH:26]=[CH:25][C:23]([O:24][CH2:2][C:3]2[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=2)=[C:20]([O:21][CH3:22])[CH:19]=1)[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 736681Ethyl FerulateHCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazine

Product 1

HCID 56929920HCID 56929920, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Adding 2-bromomethyl-3,5,6-trimethylpyrazine (0.5 g, 3.02 mmol), ferulic acid ethyl ester (0.97 g, 4.37 mmol), anhydrous potassium carbonate (1.0 g, 7.25 mmol), and DMF (40 mL) into a 100 mL three-necked bottle in turn, heating to 85° C. with oil bath, stirring to react for 8 hours, TLC [V(cyclohexane):V(ethyl acetate)=3:1 as developing agent] detecting shows that reaction is complete, (Rf of raw material=0.6, Rf of product=0.5), filtering to obtain filtrate, adding 30 mL water, extracting with chloroform (3×30 mL), incorporating the chloroform layer and wishing with water (2×20 mL), drying with anhydrous sodium sulfate, recycling chloroform under reduced pressure to obtain a light yellow oily matter, separating with a silica column, wherein eluant is V(petroleum ether):V(ethyl acetate)=3:1, collecting product, recycling the solution under reduced pressure to obtain solid, 0.75 g (E)-3-(4-((3,5,6-Trimethylpyrazin-2-yl)methoxy)-3-methoxyphenyl)acrylic acid ethyl ester, a yield is 69.7%, m.p. 111.5-111.9° C.

Workup

  1. customto react for 8 hours
  2. filtrationfiltering
  3. customto obtain filtrate
  4. extractionextracting with chloroform (3×30 mL)
  5. dry with materialdrying with anhydrous sodium sulfate
  6. customto obtain a light yellow oily matter
  7. customseparating with a silica column, wherein eluant
  8. customV(ethyl acetate)=3:1, collecting product

Sources & evidence

ORD record
ord-81129fb9b5af40a3bf64ac2b5513399e
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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