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

HRID 484193ノート

反応式

HRID 484193 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-47fcd469570a4fe8a37201780bbace37
出典データセット
uspto-grants-1993_07
特許番号
US05229510

反応ノート

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