4-Nitrophenol → 4-(3,3-Diethyl-4-oxo-2-azetidinyl)oxy-nitrobenzene

HRID 484193노트

반응식

HRID 484193 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O:14][CH:15]1[C:18]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:17](=O)[NH:16]1)(=O)C.C(OCC)(=O)C>[OH-].[Na+].CC(C)=O>[CH2:19]([C:18]1([CH2:21][CH3:22])[C:15](=[O:14])[NH:16][CH:17]1[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:20]

참가 물질

6

반응물 3

HCID 9804-NitrophenolHCID 8857Ethyl AcetateHCID 102618172-Azetidinone, 4-(acetyloxy)-3,3-diethyl-

생성물 1

HCID 197510524-(3,3-Diethyl-4-oxo-2-azetidinyl)oxy-nitrobenzene수율 80%

시약·촉매·용매 2

HCID 180Acetone용매HCID 14798Sodium Hydroxide용매

실험 절차

A solution of 4-nitrophenol (2.37 gm, 17.0 mmol) in 2.5N sodium hydroxide (6.82 mL) was added to a solution of 2-acetoxy-3,3-diethyl-4-oxoazetidine (1.05 gm, 5.7 mmol) in acetone (5 mL). After stirring at room temperature for 2.5 hours, ethyl acetate (100 mL) was added and the solution successively washed with water (3×20 mL) and saturated salt solution (20 mL). The solution was dried over anhydrous sodium sulfate and the solvent removed by rotoevaporated. The product was purified by flash column chromatography on silica gel eluted with 25% ethyl acetate in hexanes and isolated as a beige solid (1.20 gm, 80% yield): 1H-NMR δ (CDCl3) 0.94 (6H, t, J=7 Hz), 1.62-1.92 (4H, m), 5.38 (1H, s), 6.90 (2H, d, J=9 Hz), 7.66 (1H, s), 8.10 (2H, d, J= 9 Hz).

후처리

  1. washthe solution successively washed with water (3×20 mL) and saturated salt solution (20 mL)
  2. dry with materialThe solution was dried over anhydrous sodium sulfate
  3. customthe solvent removed by rotoevaporated
  4. customThe product was purified by flash column chromatography on silica gel
  5. washeluted with 25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-47fcd469570a4fe8a37201780bbace37
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05229510

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