Sodium Chloride → HCID 12014811, compound

HRID 1585165Notes

Reaction equation

HRID 1585165 reaction equation
[CH2:1]([C:4]([CH2:13][C:14]#[CH:15])(C(OC)=O)[C:5]([O:7][CH3:8])=[O:6])[C:2]#[CH:3].[Cl-].[Na+]>CS(C)=O.O.COC(C)(C)C>[CH2:1]([CH:4]([CH2:13][C:14]#[CH:15])[C:5]([O:7][CH3:8])=[O:6])[C:2]#[CH:3]

Participants

6

Reactant 2

HCID 5234Sodium ChlorideHCID 15468042,2-di-(prop-2-ynyl)-malonic acid dimethyl ester

Product 1

HCID 12014811HCID 12014811, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Dimethyl 2,2-di(2-propynyl)malonate (71 g) was treated to a Krapcho decarboxylation by heating at 170° C. with with sodium chloride (25 g) and water (23 ml) in dimethylsulfoxide (341 ml). After 15 hr, the solution was cooled and diluted with water and t-butyl methyl ether and extacted. The organic layer was washed with water (4×), brine, and then dried over sodium sulfate. Solvent removal afforded a liquid which was distilled, collecting the title compound at 109° C. (28 mm Hg).

Workup

  1. temperaturethe solution was cooled
  2. washThe organic layer was washed with water (4×), brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent removal
  5. customafforded a liquid which
  6. distillationwas distilled
  7. customcollecting the title compound at 109° C. (28 mm Hg)

Sources & evidence

ORD record
ord-756f481218f849eb804b512e03a2efa7
Source dataset
uspto-grants-1999_08
Patent number
US05936000

Reaction notes

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