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

HRID 888207Notes

Reaction equation

HRID 888207 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 14325352(2S,3R)-2-hydroxy-3-methylbutanedioic acid

Product 1

HCID 58488031(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]propanoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (2S,3R)-2-hydroxy-3-methylsuccinic acid (2.40 g; 16.2 mmol; 1.0 eq.) in acetone (80.0 mL) was added 2,2-dimethoxypropane (3.98 g; 32.4 mmol; 2.0 eq.) and copper(II) chloride (218 mg; 1.62 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 4 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 diastereoisomers) as a greenish oil (2.48 g, 82%) 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-5a92fdc3ea15442ca1eb40391bfa37c5
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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