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

HRID 1587798ノート

反応式

HRID 1587798 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 104653742-(tert-Butyldimethylsilyl)thiazole収率 65.9%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

反応条件

温度
-70 °C

実験手順

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); NMR: 0.38(6H,s), 0.97(9H,s), 7.51 (1H,d). 8.12(1H,d).

後処理

  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

出典と根拠

ORDレコード
ord-6b35afe03fd6418aadacdc8f3123d923
出典データセット
uspto-grants-1993_06
特許番号
US05219874

反応ノート

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