Isobutanol → 1016508-48-7

HRID 69944Notes

Reaction equation

HRID 69944 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:7])[CH2:5][OH:6].[Cl:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11](Cl)[N:10]=1>C1COCC1>[Cl:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]([O:6][CH2:5][CH:4]([CH3:7])[CH3:3])[N:10]=1

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

Product 1

HCID 246889781016508-48-7

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A flame-dried round bottom flask was charged with a suspension of 95% NaH (1.1 eq) in anhydrous THF (0.3 M). The stirring mixture was cooled to 0° C. in an ice-water bath and 2-methyl-1-propanol (1 eq) was added drop wise via syringe. After 30 min 2,6-dichloropyrazine (1 eq) was added, the reaction was warmed to rt and stirred for 3 h. The crude mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were washed once each with H2O and brine, then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was dissolved in CH2Cl2, loaded onto a SiO2 column, and purified by flash chromatography (9:1 hexanes/EtOAc eluent) to give 2-chloro-6-isobutoxypyrazine. LC/MS (m/z): 187.1 (MH+).

Workup

  1. temperaturethe reaction was warmed to rt
  2. customThe crude mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed once each with H2O and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe crude residue was dissolved in CH2Cl2
  9. custompurified by flash chromatography (9:1 hexanes/EtOAc eluent)

Sources & evidence

ORD record
ord-7e248a6e6395475caa42db22e817f31c
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

Loading…