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

HRID 618839

반응식

HRID 618839 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]

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

반응 조건

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 94.5% 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-4c630c3fba9043b79c5c1a3b2632f55d
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955610

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