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

HRID 49222노트

반응식

HRID 49222 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 179484394-(Chloromethyl)-2-methoxypyridine

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-398ea0ab4f274ddfb4bf56f80c405661
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706731B2

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