Thionyl Chloride → 3-(Chloromethyl)-2-isopropylpyridine

HRID 1689ノート

反応式

HRID 1689 の反応式
[CH:1]([C:4]1[C:9]([CH2:10]O)=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].S(Cl)([Cl:14])=O>C(Cl)Cl>[CH:1]([C:4]1[C:9]([CH2:10][Cl:14])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 19691012(2-Isopropylpyridin-3-yl)methanol

生成物 1

HCID 196910223-(Chloromethyl)-2-isopropylpyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

The 2-isopropyl-3-hydroxymethylpyridine (240 mg, 1.59 mmol) was dissolved in CH2Cl2 (15 mL) and cooled under nitrogen to 0° C. and thionyl chloride (1.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and saturated sodium bicarbonate. The organic layer was dried with MgSO4, filtered and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine. The 2-isopropyl-3-chloromethylpyridine (65 mg, 0.383 mmol) was dissolved in CHCl3 (10 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 150 mg) was added in small portions. The reaction was stirred for 2 hours. The solution was extracted with saturated aqueous sodium bicarbonate (2×5 mL). The organic phase was dried with MgSO4, filtered, and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 99:1 CH2Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine-N-oxide.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-4bba085d9504420e80535135054ff927
出典データセット
uspto-grants-1998_03
特許番号
US05726172

反応ノート

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