p-Toluenesulfonic acid → HCID 20394599, compound

HRID 261633Notes

Reaction equation

HRID 261633 reaction equation
C(OC([C:8]1([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH3:18][O:17][C:15]([CH2:14][CH:9]1[CH:8]([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10]1)=[O:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 20306565HCID 20306565, compound

Product 1

HCID 20394599HCID 20394599, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 800 mg quantity of 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone is dissolved in 50 ml of benzene, and 30 mg of p-toluenesulfonic acid is added to the solution. The mixture is refluxed for 30 minutes. The resulting reaction mixture is neutralized with sodium bicarbonate, and the solvent removed. The residue is purified by a silica gel column and distilled in a vacuum, giving 4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (3), R2 =CH3) in a yield of 93%, b.p. 102°-103° C./3 mm Hg.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. customThe resulting reaction mixture
  3. customthe solvent removed
  4. customThe residue is purified by a silica gel column
  5. distillationdistilled in a vacuum

Sources & evidence

ORD record
ord-37c6b030506c405783bbd01c0af83635
Source dataset
uspto-grants-1979_08
Patent number
US04166188

Reaction notes

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