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

HRID 357706

반응식

HRID 357706 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-da0c9be1ebba4849b7ce4cb8afe47ebd
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840991

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