2,2-Dimethoxypropane → (2S)-2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]propanoic acid

HRID 888210Notes

Reaction equation

HRID 888210 reaction equation
[OH:1][C@H:2]([C@H:6]([CH3:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].CO[C:13](OC)([CH3:15])[CH3:14]>CC(C)=O.[Cu](Cl)Cl>[CH3:14][C:13]1([CH3:15])[O:1][C@H:2]([C@H:6]([CH3:10])[C:7]([OH:9])=[O:8])[C:3](=[O:5])[O:4]1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 440892D-Erythro-3-Methylmalate

Product 1

HCID 58488020(2S)-2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]propanoic acidYield 59%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (2R,3S)-2-hydroxy-3-methylsuccinic acid (2.48 g; 16.8 mmol; 1.0 eq.) in acetone (80.0 mL) was added 2,2-dimethoxypropane (4.13 g; 33.6 mmol; 2.0 eq.) and copper(II) chloride (226 mg; 1.68 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 16 h at RT. The reaction mixture was evaporated and the residue taken up in CHCl3. Activated charcoal is added and the resulting mixture stirred for one hour. Filtration on a pad of celite gave the title product (mixture of diatereoisomers) as a greenish oil (1.85 g, 59%) used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated
  3. additionActivated charcoal is added
  4. stirringthe resulting mixture stirred for one hour
  5. filtrationFiltration on a pad of celite

Sources & evidence

ORD record
ord-378a66eedbe44765a7ccdb211cbcc7f1
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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