Imidazole → Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilane

HRID 1030551노트

반응식

HRID 1030551 반응식
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].[Na+].[Cl-]>CN(C)C=O>[Cl:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 5234Sodium ChlorideHCID 123612-(Chloroethoxy)ethanolHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 4555750Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilane수율 100.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Imidazole (17.8 g, 261 mmol) was dissolved in dimethylformamide (100 ml) and t-butyldimethylsilyl chloride (36.3 g, 241 mmol) was added and stirred. 2-(2-chloroethoxy)ethanol (25.0 g, 200 mmol) was added dropwise over 1 hour under cooling with ice, and the mixture was stirred for 1 further hour, left standing overnight at room temperature, and then poured into saturated aqueous NaCl (500 ml). The resulting mixture was extracted twice with ether. The extract was washed twice with saturated aqueous NaCl, and dried over MgSO4. Then the solvent was removed in vacuo, giving 1-chloro-2-(2-t-butyldimethylsilyloxyethoxy)ethane (47.8 g, 100% yield). IR (CHCl3) [cm-1 ]; 2920, 2850, 1460, 1100, 930. NMR (CDCl3) [δ ppm]; 3.94-3.90 (4 H, m) 3.79-3.72 (4 H, m), 1.05 (9 H, s), 0.22 (6 H, s).

후처리

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 1 further hour
  3. waitleft
  4. extractionThe resulting mixture was extracted twice with ether
  5. washThe extract was washed twice with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. customThen the solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-7504211e68ba4080a977dcf0ae49d6ea
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106860

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