반응 #47771

반응 방정식

aminoacetaldehyde diethyl acetal

CNBr

→

title compound

N-(2,2-Diethoxyethyl)carbodiimide

용매

ether

hexane

반응 조건

후처리

1. 1
   기타The solid was removed by filtration
2. 2
   세척washed with ether
3. 3
   농축The combined filtrate was concentrated
4. 4
   기타Purification
5. 5
   세척by column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient)

실험 절차

A solution of the aminoacetaldehyde diethyl acetal (13.16 g, 99 mmol) in ether (35 mL) was added to a suspension of CNBr (10.47 g, 99 mmol) in hexane (35 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The solid was removed by filtration and washed with ether. The combined filtrate was concentrated. Purification by column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient) afforded the title compound (7.0 g, 44.7%, one half of the starting amine served as a sacrificial base in the reaction) (Rf: 2.70, 4% methanol in dichloromethane, stain with 10% ethanolic molybdatophosphoric acid). 1H NMR 400 MHz (CDCl3) δ 4.58 (t, J=5.2 Hz, 1H), 3.77-3.69 (m, 2H), 3.65 (br, s, 1H), 3.60-352 (m, 2H), 3.16 (t, J=5.6 Hz, 1H), 1.23 (t, 6H, J=6.8 Hz).

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