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

HRID 1181208Notes

Reaction equation

HRID 1181208 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 solution 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. temperatureat reflux for 1 h
  2. customEvaporation, extraction

Sources & evidence

ORD record
ord-e110a763b6764308a6a4ecdc9ba35a24
Source dataset
uspto-grants-2007_10
Patent number
US07285543B2

Reaction notes

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