Selenium Dioxide → 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one

HRID 1597670Notes

Reaction equation

HRID 1597670 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:8])[O:5][C:6]=1[CH3:7].[Se](=O)=[O:10]>O1CCOCC1>[CH3:7][C:6]1[O:5][C:4](=[O:8])[O:3][C:2]=1[CH2:1][OH:10]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 1422104,5-Dimethyl-1,3-dioxol-2-one

Product 1

HCID 105108784-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4,5-dimethyl-2-oxo-1,3-dioxolene (1 mmol) and selenium dioxide (2.5 mmol) in dioxane was heated at reflux for 1 h. Evaporation, extraction and chromatography gave 5-methyl-4-hydroxymethyl-2-oxo-1,3-dioxolene as a yellow oil. TLC: Rf=0.5, 5% MeOH-dichloromethane.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customEvaporation, extraction and chromatography

Sources & evidence

ORD record
ord-b41a1ea1f39e42d5b9c81923e6336215
Source dataset
uspto-grants-2001_09
Patent number
US06294672B1

Reaction notes

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