Imidazole → 2-[2-(t-Butyldiphenylsilyloxy)ethylthio]ethanol

HRID 748792

반응식

HRID 748792 반응식
[S:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].N1C=CN=C1.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].C(OCC)(=O)C>ClCCl>[Si:17]([O:4][CH2:3][CH2:2][S:1][CH2:5][CH2:6][OH:7])([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 5447ThiodiglycolHCID 8857Ethyl AcetateHCID 94078tert-Butyldiphenylchlorosilane

생성물 1

HCID 597508072-[2-(t-Butyldiphenylsilyloxy)ethylthio]ethanol수율 54.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In dichloromethane (200 ml) were dissolved 2,2′-thiodiethanol (10.0 g, 81.8 mmol) and imidazole (4.70 g, 69.0 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (15.0 ml, 57.7 mmol) at room temperature. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. After concentration under reduced pressure, diethyl ether was added to the residue. Then, the insoluble matter was filtered off. The residue obtained by concentrating the filtrate under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure, whereby the title compound (11.3 g, 31.3 mmol, 54%) was obtained as a colorless oil.

후처리

  1. additionAfter completion of the dropwise addition
  2. concentrationAfter concentration under reduced pressure, diethyl ether
  3. additionwas added to the residue
  4. filtrationThen, the insoluble matter was filtered off
  5. customThe residue obtained
  6. concentrationby concentrating the filtrate under reduced pressure
  7. customthe fraction obtained from the hexane

출처 및 근거

ORD 기록
ord-b676ef213e204279a50daff62ebef92f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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