alpha5,alpha5-Dimethyl-3,5-isoxazoledimethanol → 5-(2-Hydroxypropan-2-yl)isoxazole-3-carbaldehyde

HRID 2261351Notes

Reaction equation

HRID 2261351 reaction equation
[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH2:10][OH:11])[CH:6]=1)([CH3:4])[CH3:3]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH:10]=[O:11])[CH:6]=1)([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 57736295alpha5,alpha5-Dimethyl-3,5-isoxazoledimethanol

Product 1

HCID 451179925-(2-Hydroxypropan-2-yl)isoxazole-3-carbaldehydeYield 87.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

5.38 g of [5-(1-hydroxy-1-methylethyl)isoxazol-3-yl]methanol was dissolved in 100 ml of 1,4-dioxane, and 29.74 g of manganese dioxide was then added. The mixture was stirred and heated under reflux for 10 hours. The reaction mixture was cooled to room temperature and then filtered through Celite®. The filtrate was concentrated under reduced pressure to obtain 4.63 g of 5-(1-hydroxy-1-methylethyl)-isoxazole-3-carbaldehyde.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 10 hours
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45d7122008ae4907b6071e5ce5ba8824
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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