Cesium carbonate → HCID 18798689, 화합물

HRID 356462

반응식

HRID 356462 반응식
[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

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 144161631-(4-Hydroxyphenyl)-3-phenylpropan-1-oneHCID 17859945HCID 17859945, 화합물

생성물 1

HCID 18798689HCID 18798689, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e69806be19c2469fbfa3e32de57a6628
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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