Ammonium Chloride → 1-(4-Methoxy-6-methylpyridin-2-yl)propan-2-one

HRID 1059862ノート

反応式

HRID 1059862 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH3:10])[CH:4]=1.C([Li])CCC.CN(C)[C:18](=[O:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH2:10][C:18](=[O:20])[CH3:19])[CH:4]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 157642254-Methoxy-2,6-dimethylpyridineHCID 178418339Butyllithium

生成物 1

HCID 186675641-(4-Methoxy-6-methylpyridin-2-yl)propan-2-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 4-methoxy-2,6-dimethylpyridine (1.56 g) in tetrahydrofuran (15 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 9.1 ml) dropwise at −50° C. under a nitrogen atmosphere, and the mixture was warmed to 0° C. The mixture was cooled to −50° C., and N,N-dimethylacetamide (1.59 ml) was added dropwise. Then the mixture was warmed to room temperature, poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate (100 ml×2). The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=2:1) to give 1-(4-methoxy-6-methylpyridin-2-yl)propan-2-one (1.75 g).

後処理

  1. temperatureThe mixture was cooled to −50° C.
  2. temperatureThen the mixture was warmed to room temperature
  3. extractionextracted with ethyl acetate (100 ml×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-5b93b648ca8a46579800173fe47cd2cd
出典データセット
uspto-grants-2003_02
特許番号
US06521643B1

反応ノート

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