Sulfuric Acid → HCID 20292531, compound

HRID 1395319Notes

Reaction equation

HRID 1395319 reaction equation
[OH:1][CH:2]1[CH:6]=[CH:5][C:4](=O)[CH:3]1[CH2:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][C:14]([O:16]CC)=[O:15].S(=O)(=O)(O)[OH:20].[Cl-].[Na+]>>[C:14]([CH2:13][S:12][CH2:11][CH2:10][CH2:9][CH2:8][C:3]1[C:2](=[O:1])[CH2:6][CH:5]([OH:20])[CH:4]=1)([OH:16])=[O:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 20292581HCID 20292581, compound

Product 1

HCID 20292531HCID 20292531, compound

Procedure

The solution, containing crude 3-hydroxy-2-[4-(carbethoxymethylthio)butyl]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, pmr spectrum (CDCl3): δ3.24 (singlet, --S--CH2 --CO2C2H5), 5.0 (broad singlet --CHOH--).

Workup

  1. temperatureis cooled
  2. additiontreated during 10 minutes with 75 ml
  3. temperatureThe stirred solution is refluxed for 16 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0935a2d4602c45dd85ff84a490a2577c
Source dataset
uspto-grants-1980_05
Patent number
US04202988

Reaction notes

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