Ethanol → methyl (2-oxopropoxy)acetate

HRID 652407Notes

Reaction equation

HRID 652407 reaction equation
C[C@@H:2]1[O:7][C@@H:6](OC)[C@H:5]([OH:10])[C@H:4](O)[C@H]1O.I([O-])(=O)(=O)=O.[Na+].[C:19](=[O:22])([O-])[OH:20].[Na+].[CH2:24](O)C>O>[CH3:4][C:5](=[O:10])[CH2:6][O:7][CH2:2][C:19]([O:20][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 84695Methyl α-L-rhamnopyranosideHCID 516892Sodium BicarbonateHCID 23667635Sodium periodate

Product 1

HCID 11701055methyl (2-oxopropoxy)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl-α-L-rhamnopyranoside (1.78 g, 10 mmol) in water (25 ml) was treated with sodium periodate (4.3 g) at 0° C. After 3 hours sodium hydrogen carbonate was cautiously added to neutralize the acid, the mixture was poured into ethanol (100 ml) and the insoluble material was filtered. The filtrate was concentrated to a syrup that was extracted with acetonitrile (15 ml). The extract was used for the next step without further purification.

Workup

  1. filtrationthe insoluble material was filtered
  2. concentrationThe filtrate was concentrated to a syrup that
  3. extractionwas extracted with acetonitrile (15 ml)
  4. customThe extract was used for the next step without further purification

Sources & evidence

ORD record
ord-5a2a7736657e4ff28a4755c999435469
Source dataset
uspto-grants-1987_06
Patent number
US04672057

Reaction notes

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