Reacción #91502

Ecuación de reacción

aminoacetaldehyde diethyl acetal

CNBr

→

N-(2,2-diethoxyethyl)carbodiimide

Rendimiento 45.0%

Disolventes

ether

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solid was removed by filtration
2. 2
   Lavadowashed with ether
3. 3
   ConcentraciónThe combined filtrate was concentrated

Procedimiento

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)+.

Fuente