Acetone → 2,3-O-Isopropylidene-D-ribofuranose

HRID 2112402Notes

Reaction equation

HRID 2112402 reaction equation
[O:1]=[CH:2][C@@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+].[CH3:21][C:22]([CH3:24])=O>>[CH3:21][C:22]1([CH3:24])[O:4][C@@H:3]2[C@@H:5]([C@@H:7]([CH2:9][OH:10])[O:8][CH:2]2[OH:1])[O:6]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5311110Aldehydo-D-ribose

Product 1

HCID 110087122,3-O-Isopropylidene-D-ribofuranoseYield 67.3%

Procedure

Into a suspension of D-ribose (50 g, 0.33 mol) in acetone (1500 mL) was added sulfuric acid (1 mL) dropwise. Reaction mixture was stirred overnight at room temperature and then neutralized with sat. aq. NaHCO3. Solution was decanted and concentrated. Oily residue was dissolved in EtOAc (1000 mL) and washed with water (300 mL). Aqueous layer was re-extracted with EtOAc (2×500 mL). Combined extracts were dried over Na2SO4 and concentrated to yield the target compound (42.3 g, 67.3%) as oil which was used as such for the next step.

Workup

  1. customReaction mixture
  2. customSolution was decanted
  3. concentrationconcentrated
  4. dissolutionOily residue was dissolved in EtOAc (1000 mL)
  5. washwashed with water (300 mL)
  6. extractionAqueous layer was re-extracted with EtOAc (2×500 mL)
  7. dry with materialCombined extracts were dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-53c157240f9b4279bd156a86988912db
Source dataset
uspto-grants-2009_04
Patent number
US07524825B2

Reaction notes

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