Water → 5-(((4-Hydroxyphenyl)thio)methyl)-3-methoxy-1,2-benzenediol

HRID 357706

反応式

HRID 357706 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16]C)[C:13]([O:18]C)=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][CH:3]=1.O>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([O:20][CH3:21])[C:13]([OH:18])=[C:14]([OH:16])[CH:15]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 962WaterHCID 3841364-((3,4,5-Trimethoxybenzyl)thio)phenol

生成物 1

HCID 3841385-(((4-Hydroxyphenyl)thio)methyl)-3-methoxy-1,2-benzenediol収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

3,4,5-Trimethoxybenzyl 4-hydroxyphenyl thioether (3g, 9.8 mmol) prepared as described in Example 1 was dissolved in 60 ml of dry methylene chloride, and cooled to -78° C. Then 2.8 ml (29.5 mmol) of borontribromide in 10 ml of methylene chloride was added dropwise to the above solution. After stirring for 2 hr, the solution was warmed to room temperature, and stirred for another 2 hr (monitored by TLC). Then, the reaction mixture was cooled to 0° C., and added dropwise 50 ml of water. The methylene chloride layer was separated. The crude product, obtained after drying over magnesium sulfate and concentration, was purified on silica gel column chromatography (ethyl acetate/n-hexane=2:1). 3,4-Dihydroxy-5-methoxybenzyl 4-hydroxyphenyl thioether (2.1 g, 77% yield) was obtained as a light yellow solid.

後処理

  1. temperaturethe solution was warmed to room temperature
  2. stirringstirred for another 2 hr (monitored by TLC)
  3. temperatureThen, the reaction mixture was cooled to 0° C.
  4. customThe methylene chloride layer was separated
  5. customThe crude product, obtained
  6. dry with materialafter drying over magnesium sulfate and concentration
  7. customwas purified on silica gel column chromatography (ethyl acetate/n-hexane=2:1)

出典と根拠

ORDレコード
ord-da0c9be1ebba4849b7ce4cb8afe47ebd
出典データセット
uspto-grants-1998_11
特許番号
US05840991

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