m-Chloroperbenzoic acid → 2-(Methoxycarbonyl)-3-methylpyridine 1-oxide

HRID 2201578ノート

反応式

HRID 2201578 の反応式
[CH3:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:11][O:10][C:8]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:20])=[O:9]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 12264487Methyl 3-methylpyridine-2-carboxylate

生成物 1

HCID 727140222-(Methoxycarbonyl)-3-methylpyridine 1-oxide収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of methyl 3-methylpicolinate (2 g, 14.8 mmol) and m-CPBA (3 g, 17.8 mmol) in DCM (35 mL) was stirred at RT overnight. Then the mixture was washed with NaHSO3 (a.q.) and concentrated in vacuum. The residue was purified by column chromatography (DCM:MeOH=200:1) to give the product of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (1.89 g, yield: 79%). 1H-NMR (CDCl3, 400 MHz) δ 8.05 (d, J=6.0 Hz, 1H), 7.18 (t, J=8.4 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 3.95 (s, 3H), 2.23 (s, 3H). MS (M+H)+: 168.

後処理

  1. washThen the mixture was washed with NaHSO3 (a.q.)
  2. concentrationconcentrated in vacuum
  3. customThe residue was purified by column chromatography (DCM:MeOH=200:1)

出典と根拠

ORDレコード
ord-b40c89c2bfba4f2088bb4080541338d9
出典データセット
uspto-grants-2016_06
特許番号
US09364482B2

反応ノート

読み込み中…