Sodium Chloride → HCID 44562749, compound

HRID 1732436Notes

Reaction equation

HRID 1732436 reaction equation
COC([C:5]1([CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20])[C:9](=[O:10])[CH:8]=[CH:7][CH:6]1[CH2:11][C:12]([O:14][CH3:15])=[O:13])=O.[Cl-].[Na+]>CS(C)=O.O>[CH3:15][O:14][C:12]([CH2:11][CH:6]1[CH:5]([CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20])[C:9](=[O:10])[CH:8]=[CH:7]1)=[O:13]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 70582387HCID 70582387, compound

Product 1

HCID 44562749HCID 44562749, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

A 360 mg quantity of 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone is dissolved in 8 ml of dimethyl sulfoxide containing 23 mg of water. The solution is reacted in a sealed tube with addition of 20 mg of sodium chloride. After the solution has been heated at 175° C. for 4 hours, the product is cooled to room temperature and then extracted with ethyl ether. The ethereal layer is washed, dried and distilled for the removal of the solvent. Purification of the residue by a silica gel column affords a compound (1-a) and compound (1-b) (R2 =CH3 in each). Yield of compound (1-a): 62.5%. Yield of compound (1-b): 28.5%. Combined yield: 91%. B.p. 87°-91° C./2.5 mm Hg.

Workup

  1. temperaturethe product is cooled to room temperature
  2. extractionextracted with ethyl ether
  3. washThe ethereal layer is washed
  4. customdried
  5. distillationdistilled for the removal of the solvent
  6. customPurification of the residue by a silica gel column

Sources & evidence

ORD record
ord-21f7b5764c274069828c1b70bffc324a
Source dataset
uspto-grants-1980_12
Patent number
US04237308

Reaction notes

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