Acetone → HCID 69460375, compound

HRID 1372831Notes

Reaction equation

HRID 1372831 reaction equation
[C:1]([O:9][CH2:10][C@:11]1([O:44][CH2:43][C@@H:33]([O:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:23]([O:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]1[O:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:45]C(C)=O.C(=O)([O-])[O-].[K+].[K+]>>[C:1]([O:9][CH2:10][C@:11]1([O:44][CH2:43][C@@H:33]([O:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:23]([O:24][C:25](=[O:32])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]1[O:14][C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[O:12][CH3:45])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 11093187HCID 11093187, compound

Product 1

HCID 69460375HCID 69460375, compoundYield 98%

Conditions

Temperature
50 °C

Procedure

To a solution of 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranose (10.00 g, 16.8 mmol) in acetone (40 mL) dimethyl sulfate (2.4 ml, 25.16 mmoles, 1.5 eq.) was added followed by potassium carbonate (3.48 g, 25.16 mmoles) and the reaction mixture was stirred at 50° C. under nitrogen for 18 hours. Solvents were removed under vacuo and the resulting residue was dissolved in ethyl acetate (150 ml), washed with 5% citric acid, water, brine, dried over sodium sulfate, filtered and concentrated to an oily solid. Purification on a silica gel column (hexane:ethyl acetate, 4:1) afforded 10.0 g (98%) of title compound as white foam.

Workup

  1. customSolvents were removed under vacuo
  2. dissolutionthe resulting residue was dissolved in ethyl acetate (150 ml)
  3. washwashed with 5% citric acid, water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oily solid
  7. customPurification on a silica gel column (hexane:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-004959e71cbc46f194c3f42152989677
Source dataset
uspto-grants-2007_01
Patent number
US07160867B2

Reaction notes

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