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Imidazole → 1-t-BUTYLDIMETHYLSILYLOXY-2,3-DIMERCAPTOPROPANE

HRID 636870
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HRID 636870 반응식
[SH:1][CH:2]([CH2:5][SH:6])[CH2:3][OH:4].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl-].[NH4+]>C1COCC1>[Si:12]([O:4][CH2:3][CH:2]([SH:1])[CH2:5][SH:6])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]
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참가 물질

6

반응물 4

HCID 795ImidazoleHCID 3080DimercaprolHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 212558391-t-BUTYLDIMETHYLSILYLOXY-2,3-DIMERCAPTOPROPANE수율 94.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 2,3-dimercapto-1-propanol (15.0 ml, 150 mmol) and imidazole (15.3 g, 224 mmol, 1.5 eq) in THF (300 mL) was added t-butyldimethylsilyl chloride (21.4 g, 142 mmol, 0.95 eq) at 0° C. The mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. A saturated solution of ammonium chloride was added and the aqueous phase was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulphate and the solvent was evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (90:10) to give the pure compound (32.04 g) in 94.5w yield.

후처리

  1. extractionthe aqueous phase was extracted with dichloromethane
  2. dry with materialThe organic layer was dried with anhydrous sodium sulphate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (90:10)

출처 및 근거

ORD 기록
ord-f94a4f2c8e674a8e87017adc7c2f075e
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06194576B1

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