Dimethylformamide → 4-((3,5,6-Trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acid ethyl ester

HRID 1803024Notes

Reaction equation

HRID 1803024 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])[C:16]1[CH:26]=[C:23]([O:24][CH3:25])[C:21]([OH:22])=[C:18]([O:19][CH3:20])[CH:17]=1)[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:12]([O:14][C:15](=[O:27])[C:16]1[CH:17]=[C:18]([O:19][CH3:20])[C:21]([O:22][CH2:2][C:3]2[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=2)=[C:23]([O:24][CH3:25])[CH:26]=1)[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 19845Ethyl syringateHCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazine

Product 1

HCID 594799224-((3,5,6-Trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acid ethyl esterYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Adding 2-bromomethyl-3,5,6-trimethylpyrazine (0.44 g, 0.002 mol), syringic acid ethyl ester (0.54 g, 0.0024 mol), anhydrous potassium carbonate (0.72 g, 0.005 mol), and DMF (20 mL) into a 100 mL three-necked bottle in turn, wherein the solution appears orange and turbid, irradiating with incandescent lamp, heating to 90° C., stifling to react for 12 hours, TLC [V(petroleum ether):V(ethyl acetate)=3:1 as developing agent] detecting shows that reaction is complete, (Rf of raw material=0.7, Rf of product=0.5), and the reaction solution appears deep yellow, filtering to obtain orange 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(cyclohexane):V(ethyl acetate)=3:1, collecting product, recycling the solution under reduced pressure to obtain 0.45 g light yellow 4-((3,5,6-trimethylpyrazine-2-yl)methoxyl)-3,5-dimethoxybenzoic acid ethyl ester, a yield is 61.6%, m.p. 121.7-123.2° C.

Workup

  1. customturbid, irradiating with incandescent lamp
  2. customto react for 12 hours
  3. filtrationfiltering
  4. customto obtain orange filtrate
  5. extractionextracting with chloroform (3×30 mL)
  6. dry with materialdrying with anhydrous sodium sulfate
  7. customto obtain a light yellow oily matter
  8. customseparating with a silica column, wherein eluant
  9. customV(ethyl acetate)=3:1, collecting product

Sources & evidence

ORD record
ord-9b187ff8fe8c483d8cefdec6f4fb0ed0
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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