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

HRID 1803026Notes

Reaction equation

HRID 1803026 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:25])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=1)[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:12]([O:14][C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:2][C:3]2[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=2)[CH:17]=1)[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazineHCID 15480330Ethyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 594799193-((3,5,6-Trimethylpyrazine-2-yl)methoxyl)-4-methoxybenzoic acid ethyl esterYield 71.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Adding 2-bromomethyl-3,5,6-trimethylpyrazine (0.768 g, 0.003 mol), 3-hydroxy-4-methoxybenzoic acid ethyl ester (0.954 g, 0.005 mol), anhydrous potassium carbonate (1.1 g, 0.008 mol), and DMF (60 mL) into a 100 mL three-necked bottle in turn, wherein the solution appears orange, heating to 90° C. with oil bath, stirring 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=0.6, Rf of product=0.4), and the reaction solution appears orange, 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(petroleum ether):V(ethyl acetate)=3:1, collecting product, recycling the solution under reduced pressure to obtain light yellow solid, recrystallizing with anhydrous alcohol to obtain 0.71 g 3-((3,5,6-trimethylpyrazine-2-yl)methoxyl)-4-methoxybenzoic acid ethyl ester, a yield is 60.7%, m.p. 129.8-130.4° C.

Workup

  1. customto react for 12 hours
  2. filtrationfiltering
  3. customto obtain orange 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
  9. customto obtain light yellow solid
  10. customrecrystallizing with anhydrous alcohol

Sources & evidence

ORD record
ord-0230c0434e1b48babcab62a258c3769a
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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