m-Chloroperbenzoic acid → 3-Chloromethyl-2-methyl-pyridine 1-oxide

HRID 1681

反応式

HRID 1681 の反応式
[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:15]>C(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N+:5]([O-:15])[CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 122437113-(Chloromethyl)-2-methylpyridine

生成物 1

HCID 220536063-Chloromethyl-2-methyl-pyridine 1-oxide

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a stirred solution of 3-chloromethyl-2-methylpyridine from Step 2 above (0.50 g; 3.5 mmol) in CHCl3 (40 mL) was added m-chloroperoxybenzoic acid (1.1 g of 55:45 mCPBA:mCBA; 3.5 mmol). After 1.5 h, TLC analysis indicated complete conversion to a lower Rf product. The solution was extracted with equal volumes of saturated aqueous NaHCO3 and water, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 3-Chloromethyl-2-methylpyridine N-oxide was obtained as a solid (TLC: Rf =0.30 (97:3 CH2Cl2 :MeOH); FAB MS m/z 158 (M+ +H)).

後処理

  1. extractionThe solution was extracted with equal volumes of saturated aqueous NaHCO3 and water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by pressurized silica gel column chromatography

出典と根拠

ORDレコード
ord-b8dbba8e74ff4118bc3513f530757669
出典データセット
uspto-grants-1998_03
特許番号
US05726172

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