反応 #1168077

反応方程式

3-[(tert-butyldimethylsilyloxy)methyl]-6-hydroxymethyl-1,2-dithiin

diphenylphosphoryl azide

DBU

→

azide

収率 74.5%

3-Azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]-1,2-dithiin

収率 74.5%

溶媒

toluene

toluene

反応条件

後処理

1. 1
   温度to warm up to room temperature
2. 2
   その他After 14 hours the reaction mixture was purified on a silica gel column

実験手順

To a stirred solution of 3.4 g (11.7 mmol) of 3-[(tert-butyldimethylsilyloxy)methyl]-6-hydroxymethyl-1,2-dithiin (10) in 12 mL of toluene was added diphenylphosphoryl azide (3.02 mL; 3.86 g, 14.0 mmol) in 8 mL of toluene and the solution was cooled to 0° C. To the cold solution was added dropwise 2.09 mL (2.13 g; 14.0 mmol) of DBU. The reaction mixture became dark. In 2 hours at 0° C., the reaction mixture was allowed to warm up to room temperature. After 14 hours the reaction mixture was purified on a silica gel column using 5% ethyl acetate in hexane to give 2.75 g (74.5%) of azide 15. 1H NMR (CDCl3) δ6.38 (m, 2H, C=CH), 4.30 (s, 2H, CH2O), 3.98 (s, 2H, CH2O), 0.92 (s, 9H, CCH3), 0.10 (s, 6H, SiCH3). 13C NMR (CDCl3) δ136.898 128.007, 123.471, 64.726, 55,145, 25.780, 25.735, 18.278, -5.443; MS (EI) m/z=315.1 (100%; M+).

出典