반응 #56653

반응 방정식

1-acetoxy-3-chloroacetone

1,2-bis(trimethylsilyloxy)ethane

dry ice acetone

→

title compound

수율 73.6%

(2-(Chloromethyl)-1,3-dioxolan-2-yl)methyl acetate

수율 73.6%

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The crude reaction solution
3. 3
   기타was separated by silica gel column
4. 4
   세척eluted with CH2Cl2
5. 5
   농축concentrated in-vacuo

실험 절차

A solution of 1-acetoxy-3-chloroacetone (20.0 g, 133 mmol, TCI America) and 1,2-bis(trimethylsilyloxy)ethane (30.2 g, 146 mmol, Aldrich) in anhydrous CH2Cl2 and under N2 atmosphere was cooled (−78° C., dry ice/acetone) and trimethylsilyl trifluoromethanesulfonate (1.2 mL, 6.6 mmol, Aldrich) was added. The reaction was warmed to room temperature and stirred for 5 days, with monitoring by 1H-NMR. The crude reaction solution was separated by silica gel column, and eluted with CH2Cl2, then 5% Et2O in CH2Cl2. Product fractions were pooled and concentrated in-vacuo giving the title compound (19.05 g) as a yellow oil, contaminated with 1-acetoxy-3-chloroacetone (2.93 g) and CH2Cl2 (1.0 g): 1H NMR (500 MHz, CDCl3) δ ppm 4.17 (2H, s), 4.03-4.11 (4H, m), 3.60 (2H, s), 2.09 (3H, s).

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