Water → 5-(Benzyloxy)-2-methylpyridine

HRID 358574ノート

反応式

HRID 358574 の反応式
[Na].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CO.CS(C)=O>[CH2:10]([O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 142752-Methyl-5-hydroxypyridineHCID 5360545Sodium

生成物 1

HCID 123972515-(Benzyloxy)-2-methylpyridine収率 88%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒2 回

実験手順

3.3 g of sodium were dissolved in 60 ml of methanol and stirred with 15 g of 5-hydroxy-2-methylpyridine in 230 ml of DMSO for 1 hour at a temperature of 80° to 90° C. The methanol was spun or rotated out after cooling the mixture. 23.5 g of benzylbromide were then added, followed by stirring for 20 hours at room temperature. The reaction mixture was then acidified with 2N HCL and mixed with 1500 ml of water. The mixture was then extracted with diethyl ether and the ether phase was discarded. The pH-value of the aqueous phase was then adjusted to approximately 8 and the solution was extracted with ether. The organic phase was evaporated. 24.1 g of 5-benzyloxy-2-methylpyridine were obtained. The latter was dissolved in 200 ml of glacial acetic acid, mixed with 12 ml of hydrogen peroxide (30%) and refluxed for 2 hours. The mixture was then neutralized with 40% caustic soda solution and 1000 ml of water were added. The solution was extracted with dichloromethane and the organic phase evaporated. 25 g of 5-benzyloxy-2-methylpyridine-N-oxide were obtained.

後処理

  1. temperatureafter cooling the mixture
  2. extractionThe mixture was then extracted with diethyl ether
  3. extractionthe solution was extracted with ether
  4. customThe organic phase was evaporated

出典と根拠

ORDレコード
ord-35e2cbeb83b847829fc3d6876b5d72b3
出典データセット
uspto-grants-1991_03
特許番号
US04997835

反応ノート

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