Reaktion #56653

Reaktionsgleichung

1-acetoxy-3-chloroacetone

1,2-bis(trimethylsilyloxy)ethane

dry ice acetone

→

title compound

Ausbeute 73.6%

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

Ausbeute 73.6%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe crude reaction solution
3. 3
   Sonstigewas separated by silica gel column
4. 4
   Wascheneluted with CH2Cl2
5. 5
   Einengenconcentrated in-vacuo

Vorschrift

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).

Quelle