Sulfuric Acid → HCID 20297370, compound

HRID 1395326Notes

Reaction equation

HRID 1395326 reaction equation
[OH:1][CH:2]1[CH:6]=[CH:5][C:4](=O)[CH:3]1[CH2:8][CH2:9][CH2:10][S:11][CH2:12][C:13]([O:15]CC)=[O:14].S(=O)(=O)(O)[OH:19].[Cl-].[Na+]>>[C:13]([CH2:12][S:11][CH2:10][CH2:9][CH2:8][C:3]1[C:2](=[O:1])[CH2:6][CH:5]([OH:19])[CH:4]=1)([OH:15])=[O:14]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 20297381HCID 20297381, compound

Product 1

HCID 20297370HCID 20297370, compound

Procedure

The solution, containing crude 3-hydroxy-2-[3-(carbethoxymethylthio)propyl]cyclopent-4-en-1-one, is cooled and treated during 10 minutes with 75 ml of sulfuric acid (d=1.84) with stirring. The stirred solution is refluxed for 16 hours, cooled, saturated with sodium chloride, and extracted with ethyl acetate. The extract is washed with brine, dried over magnesium sulfate, and concentrated. The residue is subjected to chromatography on silica gel with chloroform progressively enriched in ether, ether, and ether progressively enriched in acetone to afford the subject compound as an oil.

Workup

  1. temperatureis cooled
  2. temperatureThe stirred solution is refluxed for 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-750f8609f3cb4d6c9dea7188cfcb6a67
Source dataset
uspto-grants-1980_05
Patent number
US04202988

Reaction notes

Loading…