2-Bromoethanol → Bromoethylmannose

HRID 1429314Notes

Reaction equation

HRID 1429314 reaction equation
[O:1]=[CH:2][C@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[Br:13][CH2:14][CH2:15]O>CO.ClCCl>[Br:13][CH2:14][CH2:15][C:2]([C@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])=[O:1]

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 161658Demannose

Product 1

HCID 86659034Bromoethylmannose

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

DOWEX 50W×4 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 50W×4 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 rotary evaporator.

Workup

  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 rotary evaporator

Sources & evidence

ORD record
ord-d732f59a7ea64962a31efc59ea0b132b
Source dataset
uspto-grants-2015_01
Patent number
US08940690B2

Reaction notes

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