반응 #670136

반응 방정식

2-(4-bromophenoxy)ethanol

t-butyldimethylsilyl chloride

imidazole

→

crude product

수율 108.3%

[2-(4-Bromophenoxy)ethoxy](1,1-dimethylethyl)dimethylsilane

수율 108.3%

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   세척to wash these materials into the reaction flask
2. 2
   workup.ADDITIONIt was poured onto water (200 mL)
3. 3
   추출extracted with ether (3×75 mL)
4. 4
   세척The combined extracts were washed with 0.5 N HCl (200 mL), sat. NaHCO3 (200 mL), water (4×150 mL), and sat. NaCl (200 mL)
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   기타The solvent was removed under reduced pressure on a rotary evaporator

실험 절차

To a solution of [2-(4-bromophenoxy)ethanol (10.0 g, 46 mmol) in 150 mL dry dimethylformamide (30 mL) was added t-butyldimethylsilyl chloride (8.34 g, 55 mmol) and imidazole (7.82 g, 115 mmol). Additional dimethylformamide (20 mL) was used to wash these materials into the reaction flask. The resulting solution was stirred overnight at room temperature with a Newman tube. It was poured onto water (200 mL) and extracted with ether (3×75 mL). The combined extracts were washed with 0.5 N HCl (200 mL), sat. NaHCO3 (200 mL), water (4×150 mL), and sat. NaCl (200 mL), dried over MgSO4, and filtered. The solvent was removed under reduced pressure on a rotary evaporator to give the crude product (16.5 g; >100%). 1H NMR (CDCl3) d 7.34 (2H, d, J=8.9), 6.78 (2H, d, J=8.9), 4.00-3.93 (4H, m), 0.89 (9H, s), 0.08 (6H, s). 13C NMR(CDCl3) d 158.1, 132.2, 116.4, 112.8, 69.6, 61.9, 25.9, 18.4. FDMS (m/e) 330 (M+, 79Br). It was used as 100% without purification.

출처