Diethyl Ether → 2-Chloromethyl-6-phenoxypyridine

HRID 414495ノート

反応式

HRID 414495 の反応式
C(N(CC)CC)C.O[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=1.C1(C)C=CC(S([Cl:32])(=O)=O)=CC=1.C(OCC)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:32][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 128791556-Phenoxy-2-pyridinemethanol

生成物 1

HCID 138492412-Chloromethyl-6-phenoxypyridine収率 62.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
22 °C

実験手順

Triethylamine (2.27 cm3) was added portionwise to a stirred solution of 2-hydroxymethyl-6-phenoxypyridine (3 g), para-toluenesulphonyl chloride (3.7 g), and 4-dimethylaminopyridine (1.17 g) in dichloromethane (30 cm3), whilst the reaction mixture was maintained at the ambient temperature (ca. 22° C.) under an atmosphere of nitrogen. After a period of four hours, the reaction mixture was poured into diethyl ether, and washed sequentially with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried, and after removal of the solvent by evaporation under reduced pressure, the crude product was subjected to column chromatography on silica gel using dichloromethane as eluent to give 2-chloromethyl-6-phenoxypyridine (2.05 g).

後処理

  1. washwashed sequentially with saturated aqueous sodium bicarbonate, water and brine
  2. customThe organic layer was then dried
  3. customafter removal of the solvent
  4. customby evaporation under reduced pressure

出典と根拠

ORDレコード
ord-a92e87a32c644371bcfac954cf101d54
出典データセット
uspto-grants-1988_12
特許番号
US04792563

反応ノート

読み込み中…