反応 #162360

反応方程式

4-methylsulfonyloxy-2-(hydroxymethyl) butanenitrile

product

4-methylsulfonyloxy-2-(hydroxymethyl) butanenitrile

1,1-dimethylethyl (ethoxycarbonyl)azanyl carbonate

product

1,1-dimethylethyl(ethoxycarbonyl)azanyl carbonate

potassium carbonate

→

title compound

(3-cyano-3-butene-1-yl)(ethoxycarbonyl)azanyl 1,1-dimethylethyl carbonate

溶媒

water

N,N-dimethylformamide

反応条件

後処理

1. 1
   抽出extracted with diethyl ether (3×50 mL)
2. 2
   洗浄The combined organic layers were washed with water (50 mL)
3. 3
   濃縮concentrated to a pale-tan oil (10.05 g)
4. 4
   その他purified by silica gel chromatography (0-100% gradient of ethyl acetate in petroleum ether as eluant)

実験手順

A mixture of 4-methylsulfonyloxy-2-(hydroxymethyl) butanenitrile (i.e. the product of Step E) (6.87 g, 0.039 mol), 1,1-dimethylethyl (ethoxycarbonyl)azanyl carbonate (7.65 g, 0.037 mol) (i.e. the product of Step F) and potassium carbonate (10.21 g, 0.074 mol) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 20 h. The reaction mixture was poured onto iced water (100 mL) and extracted with diethyl ether (3×50 mL). The combined organic layers were washed with water (50 mL) and concentrated to a pale-tan oil (10.05 g). The oil was adsorbed onto Celite® (diatomaceous filter aid), and then purified by silica gel chromatography (0-100% gradient of ethyl acetate in petroleum ether as eluant). The appropriate fractions were combined to provide the title compound as a yellow oil (3.78 g).

出典