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

HRID 2181504ノート

反応式

HRID 2181504 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 overnight. 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) δ7.78 (d, 2H, J=7.0 Hz), 750 (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), 234 (t, 2H, J=6.2 Hz), 2.06 (m, 2H). Anal. Calc. for C25H21NO2.0.2H2O: 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 overnight
  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-5a3680db31d94e238e2b5d19c9e95027
出典データセット
uspto-grants-2005_05
特許番号
US06891044B2

反応ノート

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