Cesium carbonate → 1-[4-(2-Hydroxy-ethoxy)-phenyl]-3-phenyl-propan-1-one

HRID 1003816ノート

反応式

HRID 1003816 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:25]([OH:27])[CH3:26]>O1CCOCC1>[OH:27][CH2:25][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:17])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 144161631-(4-Hydroxyphenyl)-3-phenylpropan-1-oneHCID 178599451-Iodoethanol

生成物 1

HCID 187986891-[4-(2-Hydroxy-ethoxy)-phenyl]-3-phenyl-propan-1-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 1-(4-hydroxy-phenyl)-3-phenyl-propan-1-one from Example K (6.9 g, 30.5 mmol), and cesium carbonate (19.9 g, 61 mmol) was dissolved in dioxane (300 mL). This mixture was heated to reflux for 1 hour then treated with iodoethanol (2.85 mL, 36.5 mmol) and refluxed overnight; the reaction mixture was cooled and concentrated. The product was partitioned between EtOAc and 1N HCl. The organic layer was dried (MgSO4) and concentrated to dryness. Purification by silica gel chromatography, eluting with EtOAc:hexane (30:70 to 50:50) gave the title compound, m.p. 41-43° C. 1H NMR (CDCl3) δ 1.96 (t, 1 H), 3.02 (t, 2 H), 3.22 (t, 2 H), 3.95 (m, 2 H), 4.10 (m, 2 H), 6.92 (d, 2 H), 7.15-7.28 (m, 5 H), 7.90 (d, 2 H).

後処理

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturerefluxed overnight
  4. temperaturethe reaction mixture was cooled
  5. concentrationconcentrated
  6. customThe product was partitioned between EtOAc and 1N HCl
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated to dryness
  9. customPurification by silica gel chromatography
  10. washeluting with EtOAc:hexane (30:70 to 50:50)

出典と根拠

ORDレコード
ord-691ad9153d0e420187ca3754d3c1bb48
出典データセット
uspto-grants-2000_04
特許番号
US06046355

反応ノート

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