反応 #61197

反応方程式

imidazole-4-carbonitrile

2-(trimethylsilyl)ethoxymethyl chloride

K2CO3

acetone

→

title compound

収率 70.0%

1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile

収率 70.0%

溶媒

EtOAc

反応条件

後処理

1. 1
   洗浄washed with water (20 mL) and brine (20 mL)
2. 2
   乾燥the organic layer dried over MgSO4
3. 3
   洗浄The crude product was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane

実験手順

A flask charged with imidazole-4-carbonitrile (0.50 g, 5.2 mmol) (Synthesis, 677 (2003)) 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane to give 0.80 g (70%) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H), found 224.1. b) 2-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile

出典