Water → (NZ)-N-[1-(4-butoxyphenyl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 1629797

반응식

HRID 1629797 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH3:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:15][C:16]([S:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].O>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](=[N:21]\[S:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])/[CH3:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 3

HCID 962WaterHCID 79814Ethanone, 1-(4-butoxyphenyl)-HCID 3382465Tert-Butanesulfinamide

생성물 1

HCID 89599479(NZ)-N-[1-(4-butoxyphenyl)ethylidene]-2-methylpropane-2-sulfinamide수율 87%

시약·촉매·용매 2

HCID 178477244HCID 178477244, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a stirred solution of 1-(4-butoxyphenyl)ethanone (3 g, 15.60 mmol) and 2-methylpropane-2-sulfinamide (2.84 g, 23.41 mmol) in THF (50 mL) was added tetraethoxytitanium (8.90 g, 39.0 mmol). The reaction was heated to 70° C. for 3 d. Cold water was added and the reaction was stirred vigorously for 20 min. The mixture was filtered through Celite® and the filtrated was diluted with EtOAc. The organic solution was washed with H2O, brine, dried over MgSO4, filtered and concentrated. The crude product was by silica gel chromatography (220 g silica gel, eluted with EtOAc in hexanes) to yield the desired product (4 g, 87%) as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.88 (d, J=8.80 Hz, 2H), 6.91 (d, J=8.80 Hz, 2H), 4.02 (t, J=6.46 Hz, 2H), 2.73 (s, 3H), 1.75-1.83 (m, 2H), 1.46-1.56 (m, 2H), 1.32 (s, 9H), 0.99 (t, J=7.43 Hz, 3H).

후처리

  1. filtrationThe mixture was filtered through Celite®
  2. additionthe filtrated was diluted with EtOAc
  3. washThe organic solution was washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe crude product was by silica gel chromatography (220 g silica gel, eluted with EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a983141af41d4b7fa0dbce83c168b1d6
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791091B2

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