Sodium Hydroxide → (R)-Solketal

HRID 1793055Notes

Reaction equation

HRID 1793055 reaction equation
[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]([C@H:7]2[O:12]C(=O)[C@@H](O)[C@H]2O)[CH2:4][O:3]1.I([O-])(=O)(=O)=O.[Na+].[OH-].[Na+]>O>[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]([CH2:7][OH:12])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 108677315,6-Isopropylidene-L-gulonic acid gamma-lactoneHCID 23667635Sodium periodate

Product 1

HCID 736056(R)-Solketal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring suspension of the product of Example 32, Step B, 5,6-O-isopropylidene-L-gulono-1,4-lactone, in water is added solid sodium periodate in small portions at 3° C. to 5° C. The pH of the mixture is adjusted to 5.5 with 1N aqueous sodium hydroxide. The suspension is stirred for 2 hours at ambient temperature, then saturated with sodium chloride and filtered. To the filtrate, at 3° C. to 5° C., is added sodium borohydride in small portions. The reaction mixture is stirred for 18 hours at ambient temperature. Acetone is added to destroy the excess of sodium borohydride, and the stirring is continued for 30 minutes. The acetone is removed under reduced pressure and the aqueous residue is extracted with dichloromethane and EtOAc. The combined organic layers are dried over magnesium sulfate, filtered, and evaporated to give (R)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol.

Workup

  1. filtrationsaturated with sodium chloride and filtered
  2. additionTo the filtrate, at 3° C. to 5° C., is added sodium borohydride in small portions
  3. stirringThe reaction mixture is stirred for 18 hours at ambient temperature
  4. additionAcetone is added
  5. customto destroy the excess of sodium borohydride
  6. waitthe stirring is continued for 30 minutes
  7. customThe acetone is removed under reduced pressure
  8. extractionthe aqueous residue is extracted with dichloromethane and EtOAc
  9. dry with materialThe combined organic layers are dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-9727f0de925b491185083a8b87351762
Source dataset
uspto-grants-2006_07
Patent number
US07078438B2

Reaction notes

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