Hydrogen Peroxide → Methyl 2,3-anhydro-6,7-dideoxyheptopyranosid-4-ulose

HRID 1439382Notes

Reaction equation

HRID 1439382 reaction equation
[CH2:1]([CH:3]1[C:8](=[O:9])[CH:7]=[CH:6][CH:5]([O:10][CH3:11])[O:4]1)[CH3:2].[OH:12]O>CO>[CH3:11][O:10][CH:5]1[O:4][CH:3]([CH2:1][CH3:2])[C:8](=[O:9])[CH:7]2[O:12][CH:6]12

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 3326022H-Pyran-3(6H)-one, 2-ethyl-6-methoxy-

Product 1

HCID 13011781Methyl 2,3-anhydro-6,7-dideoxyheptopyranosid-4-uloseYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 15.6 g quantity of 2-ethyl-6-methoxy-3-oxo-3,6-dihydro-2H-pyran, 15 g of 30% aqueous solution of hydrogen peroxide and 100 ml of methanol are cooled to a temperature of about 10° C with full stirring. The same procedure as in Example 6 is thereafter followed to obtain a concentrate, which is then distilled at a reduced pressure of 3 mm Hg to give 14.8 g of 6-methoxy-4,5-epoxy-3-oxo-2-ethyltetrahydropyran as a colorless liquid fraction at 83° to 88° C in a yield of 86.3%.

Workup

  1. customto obtain a concentrate, which
  2. distillationis then distilled at a reduced pressure of 3 mm Hg

Sources & evidence

ORD record
ord-3d4e8d0f79ff47e39857774aed20fe06
Source dataset
uspto-grants-1977_11
Patent number
US04059595

Reaction notes

Loading…