Propanedioic acid, 1,3-dithiol-2-ylidene-, dimethyl ester → (1,3-Dithiol-2-ylidene)malonic acid monomethyl ester

HRID 1757304Notes

Reaction equation

HRID 1757304 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4](=[C:9]1[S:13][CH:12]=[CH:11][S:10]1)[C:5]([O:7]C)=[O:6]>CO.[OH-].[K+].CO>[CH3:1][O:2][C:3](=[O:14])[C:4](=[C:9]1[S:13][CH:12]=[CH:11][S:10]1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 9834557Propanedioic acid, 1,3-dithiol-2-ylidene-, dimethyl ester

Product 1

HCID 15432125(1,3-Dithiol-2-ylidene)malonic acid monomethyl esterYield 89.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23689386Potassium hydroxide methanolSolvent

Procedure

(1,3-Dithiol-2-ylidene)malonic acid dimethyl ester (232 mg) prepared according to the procedure described in JP-76-48666, was suspended in methanol (0.1 ml) and iN KOH/methanol (3.0 ml) was added. The reaction mixture was refluxed for 1 h and then concentrated under reduced pressure. The residue was dissolved in water and the pH of the solution was adjusted to 2 with 1N HCl. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to give the title compound (196 mg) as a pale yellow powder.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 1 h
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-93a0eaccbcb84182aefa85510d3b8f24
Source dataset
uspto-grants-1995_08
Patent number
US05444152

Reaction notes

Loading…