2-Bromoethanol → Bromoethylmannose

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.

1. washis washed with deionized water
2. customto remove color
3. temperaturethe stirred mixture heated to 80 C for 4 hours
4. customReaction
5. filtrationThe solution is filtered
6. customto remove the resin
7. washthe resin washed with ethyl acetate and DCM
8. customThe resulting filtrate is stripped to an amber oil in a rotory evaporator

ORD record

ord-bbc0ac62d8ee4f64a7a940a7b3088541

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906850B2