Potassium Carbonate → 3-[3-(Benzhydrylidene-amino)phenoxy]-cyclohex-2-enone

HRID 1862102ノート

反応式

HRID 1862102 の反応式
[C:1](=[N:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1](=[N:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][C:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 5683453-Chlorocyclohex-2-en-1-oneHCID 218772693-(Benzhydrylidene-amino)-phenol

生成物 1

HCID 218772453-[3-(Benzhydrylidene-amino)phenoxy]-cyclohex-2-enone

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A suspension of the 3-(benzhydrylidene-amino)-phenol (10.47 g, 38.3 mmol), 3-chloro-cyclohex-2-enone (5.00 g, 38.3 mmol) and potassium carbonate (5.82, 42.1 mmol) in 150 mL of acetone was heated at reflux overtight. The cooled reaction mixture was filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting hexanes/EtOAc (2:1). In this manner, 3-[3-(benzhydrylidene-amino)-phenoxy]-cyclohex-2-enone was obtained as a yellow solid, (8.82 g, 63%): 1H NMR (CDCl3) δ 7.78 (d, 2H, J=7.0 Hz), 7.50 (d, 1H, J=7.1 Hz), 7.45 (d, 2H, J=7.7 Hz), 7.34-7.10 (m, 6H), 6.69 d, 1H, J=8.0 Hz), 6.61 (d, 1H, J=8.0 Hz), 6.38 (s, 1H), 4.89 (s, 1H), 2.55 (t, 2H, J=6.2 Hz), 2.34 (t, 2H, J=6.2 Hz), 2.06 (m, 2H). Anal. Calc. for C25H21NO2 O.0.2H2O: C, 80.92; H, 5.81; N, 3.78. Found: C, 81.12; H, 5.81; N, 3.72.

後処理

  1. temperaturewas heated
  2. temperatureat reflux overtight
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluting hexanes/EtOAc (2:1)

出典と根拠

ORDレコード
ord-57c9812bcded425082ff5a95b1552787
出典データセット
uspto-grants-2003_03
特許番号
US06534524B1

反応ノート

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