Ammonium Chloride → 3-Chloro-2-methoxy-4,6-dimethylpyridine

HRID 1043894ノート

反応式

HRID 1043894 の反応式
Br[C:2]1[C:3]([CH3:12])=[N:4][C:5]([O:10][CH3:11])=[C:6]([Cl:9])[C:7]=1[CH3:8].C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Cl:9][C:6]1[C:5]([O:10][CH3:11])=[N:4][C:3]([CH3:12])=[CH:2][C:7]=1[CH3:8]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 866863283-Bromo-5-chloro-6-methoxy-2,4-dimethylpyridineHCID 178418339Butyllithium

生成物 1

HCID 866863293-Chloro-2-methoxy-4,6-dimethylpyridine収率 47.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

3-bromo-5-chloro-6-methoxy-2,4-dimethylpyridine (930 mg) was added to THF (10 mL). The solution was cooled to −78° C., and n-butyllithium (2.6 M solution in n-hexane, 1.428 mL) was added, followed by stirring at the same temperature for one hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with DCM. The organic layer was washed with brine and dried over sodium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (300 mg).

後処理

  1. extractionfollowed by extraction with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%)

出典と根拠

ORDレコード
ord-6c64f2a183194f179e74453f3fed0a5a
出典データセット
uspto-grants-2013_10
特許番号
US08563565B2

反応ノート

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