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

HRID 1170942ノート

反応式

HRID 1170942 の反応式
[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]

参加物

7

反応物 3

HCID 107842-IodophenolHCID 10796Cesium carbonateHCID 1981041'-Hydroxymethyleugenol

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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]

後処理

  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)

出典と根拠

ORDレコード
ord-c94b8e8134ec485ca4de33556529700c
出典データセット
uspto-grants-2010_11
特許番号
US07829563B2

反応ノート

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