Water → 5-[(4-Hydroxyphenyl)sulfanylmethyl]benzene-1,2,3-triol

HRID 357708

반응식

HRID 357708 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]C)[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:15]=[C:14]([OH:16])[C:13]([OH:18])=[C:12]([OH:20])[CH:11]=2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

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

생성물 1

HCID 3841395-[(4-Hydroxyphenyl)sulfanylmethyl]benzene-1,2,3-triol수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

3,4,5-Trimethoxybenzyl 4-hydroxyphenyl thioether (12 g, 39.2 mmol), prepared as described in Example 1, was dissolved in 240 ml of dry methylene chloride, and cooled to -78° C. A solution of borontribromide (18.6 ml, 195.6 mmol) in 60 ml of dry methylene chloride was added dropwise to the above solution. The mixture was warmed to room temperature, stirred overnight, cooled to 0° C., and added 300 ml of water. The aqueous layer was then extracted twice with 200 ml of ethyl acetate, dried over magnesium sulfate, concentrated and purified on silica gel column chromatography (ethyl acetate/n-hexane=2/1) to give 8.6 g (77% yield) of 3,4,5-trihydroxybenzyl 4-hydroxyphenyl thioether as a white powder.

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. temperaturecooled to 0° C.
  3. extractionThe aqueous layer was then extracted twice with 200 ml of ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. custompurified on silica gel column chromatography (ethyl acetate/n-hexane=2/1)

출처 및 근거

ORD 기록
ord-79e8c751c62f4dcdb80e8a55ae36c70e
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840991

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