Dimethylformamide → HCID 56929918, compound

HRID 1803032Notes

Reaction equation

HRID 1803032 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.[CH3:12][CH2:13][O:14][C:15](/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:13]([O:14][C:15](=[O:16])/[CH:17]=[CH:18]/[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:2][C:3]2[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=2)=[CH:23][CH:24]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 676946p-Coumaric acid ethyl esterHCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazine

Product 1

HCID 56929918HCID 56929918, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Adding 2-bromomethyl-3,5,6-trimethylpyrazine (2.15 g, 0.01 mol), p-hydroxyl ethyl cinnamate (2.30 g, 0.012 mol), anhydrous potassium carbonate (2.76 g, 0.02 mol), and DMF (50 mL) into a 100 mL three-necked bottle in turn, heating to 90° C., stifling to react for 10 hours, TLC [V(petroleum ether):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 40 mL water, extracting with chloroform (3×40 mL), incorporating the chloroform layer and wishing with water (2×30 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 2.5 g white crystalloid of (E)-3-(4-((3,5,6-Trimethylpyrazin-2-yl)methoxy)-phenyl)acrylic acid ethyl ester, a yield is 76.7%, m.p. 90-92° C.

Workup

  1. customto react for 10 hours
  2. filtrationfiltering
  3. customto obtain filtrate
  4. extractionextracting with chloroform (3×40 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-e043c03f8bf04e129ab4f21eb93dfca0
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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