Water → 2-Chloro-5-methoxy-3-methylpyridine

HRID 1758496ノート

反応式

HRID 1758496 の反応式
[H-].[Na+].[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[CH:6][N:5]=1.[CH3:12]I.O>CN(C=O)C>[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][N:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128520156-Chloro-5-methylpyridin-3-ol

生成物 1

HCID 128520162-Chloro-5-methoxy-3-methylpyridine収率 101.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Into a flame dried flask under N2 was placed DMF (150 mL), NaH (50% oil dispersion, 4.0 g, 0.08 mol) and 2-chloro-5-hydroxy-3-methylpyridine (11.7 g, 0.08 mol). The solution was stirred at 0°-5° C. until the evolution of H2 ceased and then a solution of CH3I (5.6 mL, 0.09 mol) in DMF (50 mL) was added dropwise. After the addition, the solution was allowed to stir at room temperature overnight. The resulting slurry was added to H2O and extracted with Et2O (3X). The organic layer was concentrated and the residue distilled at 85° C. (0.6 mm) to yield 12.8 g of 2-chloro-5-methoxy-3-methylpyridine (95%) as an oil; 1H NMR (CDCl3) δ 2.35 (3H, s), 3.8 (3H, s), 7.1 (1H, d, J=3) and 7.9 (1H, d, J=3 ); MS m/e (M+) 157.

後処理

  1. customInto a flame dried flask under N2
  2. additionAfter the addition
  3. stirringto stir at room temperature overnight
  4. extractionextracted with Et2O (3X)
  5. concentrationThe organic layer was concentrated
  6. distillationthe residue distilled at 85° C. (0.6 mm)

出典と根拠

ORDレコード
ord-89b3b1036985477db78a999b171f91f2
出典データセット
uspto-grants-1983_02
特許番号
US04374140

反応ノート

読み込み中…