Sodium hydride → HCID 86751260, compound

HRID 1379575Notes

Reaction equation

HRID 1379575 reaction equation
[OH:1][C:2]1([CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][CH:10]1[O:16][CH3:17])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1.[H-].[Na+].[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23]>C(Cl)Cl>[CH3:20][C:21]([CH3:26])([CH3:25])[C:22]([O:1][C:2]1([CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][CH:10]1[O:16][CH3:17])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 86751261HCID 86751261, compound

Product 1

HCID 86751260HCID 86751260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of 2-(1-hydroxy-2'methoxy-5'-bromobenzyl)pyrazine were dissolved in 15 ml of methylene chloride. At 0° C., 0.2 g of NaH were added, resulting in the evolution of a gas and formation of a precipitate. 0.4 ml of trimethylacetyl chloride were added in one portion. The reaction mixture was stirred at room temperature overnight. The solvent was then stripped from the reaction mixture, and the residue was extracted with ice water and methylene chloride. The methylene chloride layer was washed with water, dried (MgSO4), filtered and stripped of the solvent to yield 0.9 g of 3-(1-trimethylacetoxy-2'-methoxy-5'-bromobenzyl)-pyrazine.

Workup

  1. customresulting in the evolution of a gas and formation of a precipitate
  2. extractionthe residue was extracted with ice water and methylene chloride
  3. washThe methylene chloride layer was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-22baf491611d4e9cb909869a201480f9
Source dataset
uspto-grants-1997_09
Patent number
US05672567

Reaction notes

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