Reaktion #91502

Reaktionsgleichung

aminoacetaldehyde diethyl acetal

CNBr

→

N-(2,2-diethoxyethyl)carbodiimide

Ausbeute 45.0%

Lösungsmittel

ether

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solid was removed by filtration
2. 2
   Waschenwashed with ether
3. 3
   EinengenThe combined filtrate was concentrated

Vorschrift

A solution of the aminoacetaldehyde diethyl acetal (5.32 g, 40 mmol) in ether (20 mL) was added to a suspension of CNBr (4.22 g, 40 mmol) in hexane (20 mL) at RT. The reaction mixture was stirred at RT overnight. The solid was removed by filtration and washed with ether. The combined filtrate was concentrated. Flash chromatography of the concentrated residue afforded 2.82 g (45%) of the N-(2,2-diethoxyethyl)carbodiimide (a). 1H NMR (500 MHz, CDCl3): 4.58 (t, J=5.5 Hz, 1H), 3.85 (br s, 1H), 3.73 (m, 2H), 3.56 (m, 2H), 3.16 (J=5.5 Hz, 2H), 1.23 (t, J=7.0 Hz, 3H), MS: 156.8 (M−H)−; 180.9 (M+Na)+.

Quelle