Sulfuric Acid → HCID 20297370, compound

HRID 1447942Notes

Reaction equation

HRID 1447942 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 progessively enriched in ether, ether, and other 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-a895270892e84d419252d1a470fa5285
Source dataset
uspto-grants-1979_12
Patent number
US04178456

Reaction notes

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