Water → HCID 22150552, compound

HRID 703572Notes

Reaction equation

HRID 703572 reaction equation
[CH3:1][C:2]12[C:9](=NO)[CH2:8][CH:7]1[CH:6]=[CH:5][CH2:4][CH2:3]2.[OH2:12]>C(O)(=O)CCC(C)=O>[CH3:1][C:2]12[C:9](=[O:12])[CH2:8][CH:7]1[CH:6]=[CH:5][CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 962WaterHCID 86744483HCID 86744483, compound

Product 1

HCID 22150552HCID 22150552, compound

Reagents, catalysts & solvents 1

HCID 11579Levulinic AcidSolvent

Procedure

A solution of 120 mg of 6-methylbicyclo[4.2.0]oct-2-en-7-one oxime, prepared as shown in Preparation 19, in 4 ml of levulinic acid/1N hydrochloric acid (9/1) was stirred at room temperature for 48 hours. The mixture was poured into water and extracted with hexane. The combined hexane extracts were washed with saturated sodium bicarbonate, brine and dried over anhydrous sodium sulfate. Solvent was carefully removed under reduced pressure, and the residue chromatographed on silica gel, eluting with 10% ethyl acetate in hexane, to give 6-methylbicyclo[4.2.0]oct-2-en-7-one, the compound of formula (8).

Workup

  1. extractionextracted with hexane
  2. washThe combined hexane extracts were washed with saturated sodium bicarbonate, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customSolvent was carefully removed under reduced pressure
  5. customthe residue chromatographed on silica gel
  6. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-510f45b2526042208d50d4d607aacaae
Source dataset
uspto-grants-1991_01
Patent number
US04983627

Reaction notes

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