Reacción #167507

Ecuación de reacción

D-mannose

2-bromoethanol

→

Bromoethylmannose

Disolventes

methanol dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadois washed with deionized water
2. 2
   Otroto remove color
3. 3
   Temperaturathe stirred mixture heated to 80 C for 4 hours
4. 4
   OtroReaction
5. 5
   FiltraciónThe solution is filtered
6. 6
   Otroto remove the resin
7. 7
   Lavadothe resin washed with ethyl acetate and DCM
8. 8
   OtroThe resulting filtrate is stripped to an amber oil in a rotory evaporator

Procedimiento

DOWEX 50Wx4 resin (Alfa Aesar, Ward Hill, Mass.) is washed with deionized water to remove color. A mixture of 225 gm D-mannose (1.25 mol; 1 equiv., Alfa Aesar) and 140 gm DOWEX 50Wx4 is treated with 2.2 L 2-bromoethanol (30.5 mol, 25 equiv.; 124.97 gm/mol; 1.762 gm/mL; BP=150 C; Alfa Aesar) and the stirred mixture heated to 80 C for 4 hours. The reaction is monitored by TLC (20% methanol/dichloromethane (DCM)). Reaction is complete after about four hours, and then allowed to cool to room temperature. The solution is filtered to remove the resin, and the resin washed with ethyl acetate and DCM. The resulting filtrate is stripped to an amber oil in a rotory evaporator.

Fuente