Isobutanol → 2-chloro-6-(2-methylpropoxy)pyrazine

HRID 69944ノート

反応式

HRID 69944 の反応式
[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

参加物

5

反応物 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

生成物 1

HCID 246889782-chloro-6-(2-methylpropoxy)pyrazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-7e248a6e6395475caa42db22e817f31c
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

反応ノート

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