tert-Butyldimethylsilyl chloride → 2-(tert-Butyldimethylsilyl)thiazole

HRID 1655076노트

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HRID 1655076 반응식
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[C:12]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>CCOCC>[Si:16]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:18])[CH3:17]

참가 물질

6

반응물 4

HCID 28928tert-Butyldimethylsilyl chlorideHCID 764302-BromothiazoleHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

생성물 1

HCID 104653742-(tert-Butyldimethylsilyl)thiazole수율 65.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
-70 °C

실험 절차

A solution of 2-bromothiazole (57.4 g) in ether (70 ml) was added slowly to a solution of n-butyllithium (1.6M solution in hexane, 241 ml) in ether (700 ml) under an atmosphere of argon, maintaining the temperature below -60° C. After stirring for 1 hour at -70° C., a solution of tert-butylchlorodimethylsilane (63.0 g) in ether (70 ml) was added slowly dropwise. The reaction mixture was then allowed to warm to ambient temperature and stirred for 16 hours. Saturated aqueous sodium bicarbonate solution was added, the layers were separated, and the aqueous phase extracted twice with ether. The combined organic phases were dried (MgSO4), concentrated, and the residue was purified by column chromatography, eluting with 25% ethyl acetate/hexane (v/v), and subsequent distillation to give 2-tert-butyldimethylsilylthiazole (Q) (46 g, 58% yield) as an oil (b.p. 88°-96° C. at 10 mm of mercury);

후처리

  1. temperaturemaintaining the temperature below -60° C
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 16 hours
  4. customthe layers were separated
  5. extractionthe aqueous phase extracted twice with ether
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated
  8. customthe residue was purified by column chromatography
  9. washeluting with 25% ethyl acetate/hexane (v/v), and subsequent distillation

출처 및 근거

ORD 기록
ord-e9c52635d1ad44c3824294bdbd1bad08
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05410064

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