2-Iodophenol → 1-(3,4-Dimethoxyphenyl)-3-(2-hydroxyphenyl)propan-1-one

HRID 1170942노트

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HRID 1170942 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:14])[CH:12]=[CH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:14])[CH2:12][CH2:13][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

7

반응물 3

HCID 107842-IodophenolHCID 10796Cesium carbonateHCID 1981041'-Hydroxymethyleugenol

생성물 1

HCID 595536751-(3,4-Dimethoxyphenyl)-3-(2-hydroxyphenyl)propan-1-one수율 45%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of 1-(3,4-dimethoxy-phenyl)-prop-2-en-1-ol (236 mg, 1.22 mmol) in THF (2 mL) was added under a nitrogen atmosphere 2-iodophenol (267 mg, 1.22 mmol), cesium carbonate (158 mg, 0.47 mmol) and palladium(II) acetate (8 mg, 0.04 mmol). The reaction mixture was stirred for 4 h at 80° C. After cooling to ambient temperature it was diluted with ethyl acetate (10 mL) and washed with water (10 mL) and brine (10 mL). The aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=90:10 to 60:40) afforded the title compound (155 mg, 45%) as a colourless oil. MS m/e: 285.0 [M−H]

후처리

  1. temperatureAfter cooling to ambient temperature it
  2. washwashed with water (10 mL) and brine (10 mL)
  3. extractionThe aqueous layers were extracted with ethyl acetate (10 mL)
  4. dry with materialthe combined organic layers dried over sodium sulfate
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=90:10 to 60:40)

출처 및 근거

ORD 기록
ord-c94b8e8134ec485ca4de33556529700c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829563B2

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