Thionyl Chloride → 4-(Chloromethyl)-2-methoxypyridine

HRID 49222ノート

反応式

HRID 49222 の反応式
O=S(Cl)[Cl:3].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13]O)[CH:10]=[CH:9][N:8]=1>C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13][Cl:3])[CH:10]=[CH:9][N:8]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 14462410(2-Methoxypyridin-4-yl)methanol

生成物 1

HCID 179484394-(Chloromethyl)-2-methoxypyridine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

1.57 ml (21.6 mmol) of SOCl2 are added dropwise, whilst cooling with ice and under a N2 atmosphere, to a solution of 1.5 g (10.8 mmol) of 2-methoxy-4-(hydroxymethyl)-pyridine [for preparation see J. Org. Chem. 54 (1989), 5580] in 13 ml of chloroform. After 16 h at RT, the mixture is concentrated by evaporation, water and 2N sodium hydroxide solution are added to the residue, and extraction immediately takes place 3 times with chloroform. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form 2-methoxy-pyridin-4-yl-methylchloride; 1H NMR (CDCl3) δ8.15 (d, 1H), 6.90 (d, 1H), 6.76 (s, 1H), 4.49 (s, 2H), 3.94 (s, H3C).

後処理

  1. concentrationthe mixture is concentrated by evaporation, water and 2N sodium hydroxide solution
  2. additionare added to the residue, and extraction immediately takes place 3 times with chloroform
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-398ea0ab4f274ddfb4bf56f80c405661
出典データセット
uspto-grants-2004_03
特許番号
US06706731B2

反応ノート

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