Sulfuric Acid → HCID 20292531, compound

HRID 1413576Notes

Reaction equation

HRID 1413576 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+]>>[OH:20][CH:5]1[CH2:6][C:2](=[O:1])[C:3]([CH2:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4]1

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 about 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 chromatographed on silica gel and is eluted 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, --SCH2CH3) 5.0 (broad singlet, --CHOH--), and 7.38 (singlet, vinyl hydrogen).

Workup

  1. temperatureis cooled
  2. temperatureThe stirred solution is refluxed for about 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel
  8. washis eluted with chloroform

Sources & evidence

ORD record
ord-99cac988c0e04b3eb427c5d0e95decad
Source dataset
uspto-grants-1981_02
Patent number
US04250325

Reaction notes

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