m-Chloroperbenzoic acid → HCID 86702132, 화합물

HRID 1776183노트

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HRID 1776183 반응식
[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]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 86702131HCID 86702131, 화합물

생성물 1

HCID 86702132HCID 86702132, 화합물수율 26.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
40 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-00784c6cbd404a48952a727b3cb675a1
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265772B2

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