Sodium Methoxide → Methyl 2,6-dichloro-4-methoxynicotinate

HRID 80829ノート

反応式

HRID 80829 の反応式
[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8](Cl)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][O-:15].[Na+]>CO>[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]([O:15][CH3:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 71304377Methyl 2,4,6-trichloronicotinate

生成物 1

HCID 86690279Methyl 2,6-dichloro-4-methoxynicotinate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 2,4,6-trichloronicotinate [(5.04 g, 20.96 mmol), prepared as described in WO2010/31589] in methanol (52 mL) was added the sodium methoxide (25 wt % in methanol, 5.04 mL, 22.0 mmol) at room temperature. The cloudy white mixture was stirred for 17 h, then partitioned between EtOAc and water. The layers were separated and the aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by FCC (0-20% EtOAc:heptane) to provide methyl 2,6-dichloro-4-methoxynicotinate. MS (ESI+) m/z 236.1 (M+H)+.

後処理

  1. custompartitioned between EtOAc and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by FCC (0-20% EtOAc:heptane)

出典と根拠

ORDレコード
ord-66422f9133814f869d803f2cca1e4769
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

反応ノート

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