HCID 54721418, compound → 6-Ethyl-4-hydroxy-2H-pyran-2-one

HRID 1252718Notes

Reaction equation

HRID 1252718 reaction equation
C([C:5]1[C:6](=[O:17])[O:7][C:8]([CH2:15][CH3:16])=[C:9](C(O)=O)[C:10]=1[OH:11])(=O)CC>S(=O)(=O)(O)O.O>[OH:11][C:10]1[CH:9]=[C:8]([CH2:15][CH3:16])[O:7][C:6](=[O:17])[CH:5]=1

Participants

4

Reactant 1

HCID 54721418HCID 54721418, compound

Product 1

HCID 547135586-Ethyl-4-hydroxy-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-propionyl-4-hydroxy-5-carboxy-6-ethyl-2-pyrone (7 gm) in concentrated sulphuric acid (14 ml) and water (2 ml) was heated in an oil bath set at 120° C. for 2 hours. The solution was cooled and then poured into ice. The insoluble solid was filtered. The filtrate was extracted with ethyl acetate (3×100 ml). The combined organic layer was dried over magnesium sulphate and evaporated to give a dirty brown solid. The combined solid from the filtration and the extraction was purified by flash column chromatography (Whatman LPS-II silica gel, elution gradient: 40 to 80% ethyl acetate:pet. ether 30-60) to give 4-hydroxy-6-ethyl-2-pyrone, which was further purified by recrystallization from ether. (Yield: 2.7 gm), m.p. 106°-108° C.

Workup

  1. temperatureThe solution was cooled
  2. additionpoured into ice
  3. filtrationThe insoluble solid was filtered
  4. extractionThe filtrate was extracted with ethyl acetate (3×100 ml)
  5. dry with materialThe combined organic layer was dried over magnesium sulphate
  6. customevaporated
  7. customto give a dirty brown solid
  8. filtrationThe combined solid from the filtration
  9. extractionthe extraction
  10. customwas purified by flash column chromatography (Whatman LPS-II silica gel, elution gradient: 40 to 80% ethyl acetate:pet. ether 30-60)

Sources & evidence

ORD record
ord-2850d0b1fb5445ff966f7aaa6be69b7a
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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