Sodium sulfate decahydrate → (4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

HRID 1785291Notes

Reaction equation

HRID 1785291 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8](OC)=[O:9])[CH2:4][O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][CH2:8][OH:9])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 11073901(R)-Methyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11480522(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolaneYield 93.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.0 g of methyl 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)acetate in 29 ml of diethyl ether, 110 mg of lithium aluminum hydride was added under cooling with ice, followed by 12 hours' stirring at the same temperature. Sodium sulfate decahydrate was added to the reaction liquid which was then stirred for 30 minutes and filtered with Celite. Distilling the solvent off under reduced pressure, 782 mg of the title compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. stirringwas then stirred for 30 minutes
  3. filtrationfiltered with Celite
  4. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-37614793e01048b6aa3def03b23c9708
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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