2-Methyl-5-hydroxypyridine → 2-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine

HRID 550423ノート

反応式

HRID 550423 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[CH3:21]>CC(N(C)C)=O>[CH3:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[CH3:21])=[CH:9][N:8]=1

参加物

5

反応物 3

HCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydrideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

生成物 1

HCID 179901022-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine収率 98%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

実験手順

Sodium hydride (25.6 g, 60% dispersion in oil, 0.64 mol) was added portion-wise to a solution of 5-hydroxy-2-methylpyridine (70 g, 0.64 mol) in DMA (700 ml) while keeping the temperature below 40° C. At the end of the addition, the mixture was stirred at room temperature for 1 hour and 2-fluoro-5-nitrotoluene (91.3 g, 0.59 mol) in DMA (100 ml) was added slowly. The mixture was stirred at 80° C. for 3 hours and then cooled. The solvents were evaporated under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over MgSO4. After evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 30% ethyl acetate in petroleum ether) to give 2-methyl-5-(2-methyl-4-nitrophenoxy)pyridine as an oil (141 g, 98%); NMR spectrum (CDCl3): 2.43 (s, 3H), 2.59 (s, 3H), 6.74 (d, 1H), 7.21 (d, 1H), 7.27 (d, 1H), 8.00 (d, 1H), 8.17 (s, 1H), 8.32 (s, 1H).

後処理

  1. customthe temperature below 40° C
  2. additionAt the end of the addition
  3. stirringThe mixture was stirred at 80° C. for 3 hours
  4. temperaturecooled
  5. customThe solvents were evaporated under vacuum
  6. customthe residue was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over MgSO4
  9. customAfter evaporation of the solvents
  10. customthe residue was purified by chromatography on silica gel (eluant: 30% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-6915a1bafa16496eb928f2e978db9d92
出典データセット
uspto-grants-2011_05
特許番号
US07947676B2

反応ノート

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