2-Methoxyethanol → HCID 86690871, compound

HRID 1465568Notes

Reaction equation

HRID 1465568 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][O:10][CH2:11][CH2:12][OH:13].CC(C)([O-])C.[Na+]>C1COCC1>[Br:8][C:5]1[CH:4]=[N:3][C:2]([O:13][CH2:12][CH2:11][O:10][CH3:9])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 114704212,5-dibromopyrazineHCID 23676156Sodium t-butoxide

Product 1

HCID 86690871HCID 86690871, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,5-dibromopyrazine (22-1, 20.0 g, 84.1 mmol), 2-methoxyethanol (6.40 g, 84.1 mmol), and sodium tert-butoxide (11.3 g, 118 mmol) in 168 mL of THF was stirred at room temperature overnight. The solution was concentrated under reduced pressure and added with ethyl acetate. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc:hexanes=1:5 as eluant) to give 2-bromo-5-(2-methoxyethoxy)pyrazine (22-2, 17.2 g) as yellow oil in 88% yield: 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=1.0 Hz, 1 H), 8.07 (d, J=1.0 Hz, 1 H), 4.46 (t, J=5.0 Hz, 2 H), 3.74 (m, 2 H), 3.43 (s, 3 H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionadded with ethyl acetate
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (EtOAc:hexanes=1:5 as eluant)

Sources & evidence

ORD record
ord-067737d553bb4bab9c2b0b6ebc1449b7
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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