m-Chloroperbenzoic acid → HCID 86702132、化合物

HRID 1776183ノート

反応式

HRID 1776183 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH2:12][C:13]([CH3:15])=[CH2:14])[S:8]([CH3:11])(=[O:10])=[O:9].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH2:12][C:13]1([CH3:15])[CH2:14][O:24]1)[S:8]([CH3:11])(=[O:10])=[O:9]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 86702131HCID 86702131、化合物

生成物 1

HCID 86702132HCID 86702132、化合物収率 26.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
40 °C

実験手順

To a stirring solution of N-(furan-2-ylmethyl)-N-(2-methylallyl)methanesulfonamide (1.0 g, 4.3 mmol) in anhydrous methylene chloride (20 mL) was added 3-chloroperbenzoic acid (70%, 2.1 g, 8.6 mmol). The mixture was stirred at ambient temperature for 2 hours and at 40° C. for 18 hours. The mixture was diluted with methylene chloride and successively washed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions. The organic layer was dried (anhydrous sodium sulfate), filtered, and concentrated. The crude residue was purified by silica gel column chromatography (10-60% ethyl acetate in hexanes) to give a clear oil (0.278 g, 26%). 1H NMR (CDCl3, 300 MHz) δ 7.40-7.35 (dd, 1H, J=0.9, 1.8 Hz), 6.33-6.30 (m, 2H), 4.52-4.51 (m, 2H), 3.48-3.43 (d, 1H, J=15 Hz), 3.13-3.09 (d, 1H, J=15 Hz), 2.73-2.72 (d, 1H, J=4.5 Hz), 2.70 (s, 3H), 2.62-2.61 (d, 1H, J=4.5 Hz), 1.35 (s, 3H).

後処理

  1. washsuccessively washed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions
  2. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel column chromatography (10-60% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-00784c6cbd404a48952a727b3cb675a1
出典データセット
uspto-grants-2016_02
特許番号
US09265772B2

反応ノート

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