Acetone → HCID 178481590, compound

HRID 223425Notes

Reaction equation

HRID 223425 reaction equation
[CH3:1][C:2]([C:5]1[O:9][N:8]=[C:7]([N:10]2[CH:14]([OH:15])[CH:13]([OH:16])[N:12]([CH3:17])[C:11]2=[O:18])[CH:6]=1)([CH3:4])[CH3:3].CC(C)=O>Cl(O)(=O)(=O)=O.O>[CH2-:2][C:5]([CH3:6])=[O:9].[CH3:4][C:2]([C:5]1[O:9][N:8]=[C:7]([N:10]2[CH:14]([OH:15])[CH:13]([OH:16])[N:12]([CH3:17])[C:11]2=[O:18])[CH:6]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 180AcetoneHCID 12918841HCID 12918841, compound

Product 1

HCID 178481590HCID 178481590, compound

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 962WaterSolvent

Procedure

To a solution of 1.0 gram of 3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-4,5-dihydroxy-1-methyl-2-imidazolidinone in 20 ml. of anhydrous acetone were added three drops of 70% perchloric acid. The reaction mixture stood at ambient temperature for sixteen hours, and then was diluted with 100 ml. of water. The white crystalline precipitate was collected by filtration and recrystallized from diethyl ether and hexane to afford 3-[5-(1,1-dimethylethyl)-3-isoxazolyl]4,5-dihydroxy-1-methyl-2-imidazolidinone acetonide. M.P. 157°-159° C. Mass Spectrum M+Theory 295; Found 295.

Workup

  1. waitThe reaction mixture stood at ambient temperature for sixteen hours
  2. additionwas diluted with 100 ml
  3. filtrationThe white crystalline precipitate was collected by filtration
  4. customrecrystallized from diethyl ether and hexane

Sources & evidence

ORD record
ord-2b8986e1e1d94d508231d76940c60c38
Source dataset
uspto-grants-1982_10
Patent number
US04354030

Reaction notes

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